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DOI: 10.1055/a-1758-6312
Dual Role of the Arylating Agent in a Highly C(2)-Selective Pd-Catalysed Functionalisation of Pyrrole Derivatives
This research was funded by the Ministry of Education, Science and Technological Development, Republic of Serbia through Grant Agreement with the University of Belgrade-Faculty of Pharmacy No: 451-03-9/2021-14/200161.
Abstract
Pyrrole derivatives with C(2)-aryl substituents are an important and widespread class of heterocyclic compounds. Their synthesis can be accomplished using several strategic variants which usually entail either protection of the N–H functionality followed by the arylation, or a direct arylation. Although direct arylation is a preferable process due to a reduced number of synthetic steps, it often requires vigorous conditions or challenging reagents. To this synthetic repertoire, we add a novel method that is based on the dual role of the arylating agent. It serves as the nitrogen protecting group while also being involved in the arylation step. Deprotection as a final stage is carried out simultaneously utilising amines as reacting components. This approach ensures relatively mild conditions and exclusive C(2) selectivity yielding 2-arylpyrroles with the amide functionality. While aromatic amines are not suitable partners under studied conditions, most likely due to lower nucleophilicity, aliphatic amines, either primary or secondary, afford products in good yields.
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Since its discovery in the mid 19th century, pyrrole has been one of the central cores in heterocyclic chemistry.[1] Together with its benzo analogues, these compounds comprise an immense group of important organic derivatives that exhibit a variety of interesting biological and chemical properties.[2] The pyrrole ring is one of the most explored heterocycles in drug discovery programs as well, with derivatives showing antibacterial, antipsychotic, antitumor, anti-inflammatory, and analgesic activities, to mention just a few.[3] Currently, more than twenty marketed pharmaceuticals contain a pyrrole nucleus.[4] It is also a constitutional component of many natural products while the tetrapyrrole scaffold is a key structural unit of biologically important heme and related porphinoid co-factors such as chlorophyll a, vitamin B12 and others.[5] Pyrrole and its derivatives are also structural elements of polymers, dyes, optoelectronic materials, high-performance semiconductors and glucose sensors.[6] This significance of pyrroles in many areas makes this class of compounds constantly attractive synthetic targets, and novel routes for their preparation are often reported in the literature.[7] Consequently, the number of available synthetic methodologies is immense, from venerable Pall–Knorr synthesis to modern transition-metal-promoted transformations.
Pyrrole derivatives possessing an aryl substituent at C(2) are an important class of heterocyclic compounds particularly in medicinal chemistry.[8] There are several drugs on the market retaining this structural feature (Figure [1]), including atorvastatin (1),[9] a cholesterol-lowering agent, or rucaparib (2),[10] a PARP inhibitor used as an anticancer agent. Biarylpyrroles 3 and 4 were found to exhibit EP1 receptor antagonist activity and anticoccidial activity respectively, while triaryl-1H-pyrrole 5 is an important antihyperglycemic agent acting as an inhibitor of glucagon receptor.[11] The 2-arylpyrrole scaffold can also be found in some fluorescence dyes and pesticides.[12]
The broad spectrum of properties of 2-arylpyrroles has encouraged the development of many strategies for their direct synthesis which do not rely on C(2)-prefunctionalised derivatives such as halides or pseudohalides. One approach is based on the palladium-catalysed arylation utilising preformed pyrrole metal salts in order to eliminate the interference of the NH functionality with the C(2) functionalisation (Scheme [1a]).[13] The main drawbacks of this approach are its considerable moisture sensitivity and its limited functional group tolerance owing to the presence of the N-M moiety. An alternative approach depends on the utilisation of standard N-protecting or masking groups to obtain C(2)/C(3) site-selectivity in the arylation step (Scheme [1b]). Based on this strategy different methods for the arylation of N-protected and N-alkylated pyrroles have been developed over the years, including Pd-, Cu- or Rh-catalysed transformations.[14] Employment of protecting groups adds two additional steps to the reaction sequence, therefore chemical transformations that can be performed on free N-H pyrroles represent an attractive strategic approach. In recent years, several such methods have been reported (Scheme [1c]). Generally, most of them employed palladium catalysts and base in combination with an aryl halide and relatively high temperatures[15] or diaryliodonium salts at room temperature.[16] Some methods utilised other metal catalysts such as those centred around Rh,[17] Ru,[18] Co[19] or Fe.[20] Other methods are based on palladium-catalysed arylation with arylboronic acids[21] or the use of diaryliodonium salts[22] with a strong base and without transition-metal catalysts. Although these are valuable synthetic tools, they occasionally suffer from notable drawbacks, including the requirement for very high temperatures or/and long reaction times (typically 120–200 °C for 18–48 h, or 100 °C/sealed tube), the need for strong bases or directing group to achieve selectivity, and non-availability of arylating agents. Moreover, the formation of biphenyls has been observed in some cases, while some methods require significant excess of pyrrole to obtain a satisfactory yield of the product.
To these strategies for the arylation of pyrroles at C(2), we add a novel process that combines formal N-protection/C(2)-arylation with simultaneous removal of the protecting group. In other words, the arylating agent plays the role of N-H protecting group, thereby allowing both processes, arylation and deprotection, to be carried out simultaneously under mild conditions (Scheme [1]). Exclusive C(2) selectivity is a result of the close proximity of the arylating moiety attached to N(1). Furthermore, timely deprotection in the reaction sequence is ensured by balanced leaving group properties of the pyrrole ring.
During the study of the dearomatisation processes of pyrrole derivatives, we discovered the transformation outlined in Scheme [2]. In an attempt to perform intramolecular arylation of pyrrole 6a at C(2) in the presence of secondary amine, a clean formation of bisaryl product 7 in 64% yield was observed. This simple transformation obviously proceeds via arylation/amidation sequence and it can be an alternative route to approach b outlined in Scheme [1], but with some advantages. Namely, since the transformation presented in Scheme [2] utilises the arylation reactant as a protecting group as well, it simplifies the synthetic process and purification procedure, while the reaction is carried out under relatively mild conditions. In addition, the arylation of this type may proceed only via C(2) functionalisation of pyrrole, thus eliminating any potential issues on C(2)/C(3) selectivity.
The process delineated in Scheme [2] may take place in two ways, depending on the order of arylation/amidation sequence. If the intramolecular arylation precedes the amidation, fused system 8 should be formed, and then undergo amidation with consequent ring-opening (Scheme [3], pathway a). An alternative path proposes amidation as the first step to generate pyrrole and iodoamide 9, which then react in an intermolecular fashion to afford the final product (Scheme [3], pathway b). Based on the current literature results, pathway b seems to be less likely and would probably require different, rather more vigorous, reaction conditions to perform the intermolecular arylation on the NH-pyrrole.
Nevertheless, we performed several experiments intending to ascertain the nature of this process (Scheme [4]). When the amine component was omitted from the reaction mixture, we observed exclusive formation of fused system 8 in quantitative yield. Upon isolation of this compound and after its exposure to benzylamine in MeCN at reflux, compound 10 was isolated in 78% yield. Attempts to perform direct intermolecular arylation of pyrrole using amide 11, under conditions we employed typically in the reaction outlined in Scheme [2], afforded product 7 but only in 16% yield after 24 hours. Finally, when the reaction process was intercepted after 6 hours, analysis of the 1H NMR spectrum of the reaction mixture showed the presence of fused system 8 and product 7 in a 15:85 ratio. We performed the same reaction with imidazole derivative 6b and morpholine, but in this instance the only isolated product was amide 11.
Based on all these results, it is clear that the first step of this reaction is intramolecular arylation followed by the ring-opening via amidation. It seems that differences in the reaction rates between the intramolecular arylation and potential transformation involving 6a and the amine to produce pyrrole and amide 11 is sufficient to fully favor the first process. This was confirmed by careful examination of the 1H NMR spectrum of the crude reaction mixture which did not show the formation of these products. Reactivity of the imidazole derivative 6b, which produced cleanly amide 11, supported our observation that the process is controlled by a fine balance in reaction rates of the Pd-catalysed cyclisation and the nucleophilic acyl substitution. Incorporation of an additional nitrogen (6a to 6b) into the amide moiety, which makes the amino component of the amide a better leaving group, increased its reactivity sufficiently, favoring the acyl substitution as the first step.
We further examined the reaction scope as outlined in Table [1]. Pyrrole derivative 6a was used in the arylation process under the above-described conditions using various amines. All secondary amines (Table [1], entries f, h, i) afforded expected products 13f,h,i in synthetically acceptable yields ranging from 60% to 76%. Primary amines were mainly equally efficient (entries a–d) producing bisaryl products 13a–d in comparable yields. Exceptions are allylamine and aminoethanol (entries e and g) which afforded products 13e and 13g in 48% and 41% yields, respectively. Functionalities in these amines have the potential to interfere with the Pd-catalysed arylation step, which may have caused a slight decrease in the reaction yields. The reaction of pyrrole 12a, a derivative of nitrobenzoic acid, suggested that the presence of substituents at the acid residue can be tolerated (entry j). In this case, the oxidative addition of Pd(0) might be more efficient, but at the same time, the pyrrole amide might be more susceptible to the nucleophilic attack. Nonetheless, the reaction rates were not considerably perturbed and product 13j was isolated in 73% yield. An additional example with starting material 12b incorporated the naphthoic acid residue in these processes with reasonable efficacy (entry k). Finally, the described methodology was used for functionalisation of the indole ring. Under the described conditions, indole derivatives 12c and 12d proved to be as efficient as pyrrole derivatives and afforded the expected product 13l and 13m in 74% and 76% yields (entries l, m).
a Reaction conditions: 6a or 12 (0.1 mmol), amine (0.3 mmol), K3PO4 (0.15 mmol), Pd(OAc)2 (0.01 mmol), Ph3P (0.02 mmol), MeCN (5 mL), reflux, 6 h.
During the course of this study, we also used anilines such as 3,5-dimethyl- and 2,4-dimethylaniline as amino components. With 6a as a starting compound, under the standard described conditions these amines did not afford the expected products. The formation of fused system 8 was the only observed process. The products were not formed with N-aminoethylpiperazine and ethylenediamine as the amino components either. In these cases, the chelating amines possibly obstructed the initial Pd-promoted cyclisation and the starting materials were the only observed constituents of the reaction mixtures. We also briefly explored the possible functionalisation of tryptophan-protected derivative 14 (Scheme [5]). Surprisingly, the only product formed was the cyclic indole derivative 15 in 88% yield. Currently, it is not clear how the substituent at C(3) affects the ring-opening process, but its role seems to be detrimental for the reactivity of 14.
In conclusion, we have developed a novel methodology for the selective arylation of pyrrole derivatives utilising the arylating agent to perform a dual role, the protection of NH moiety and the C(2) arylation. Easily accessible N-acylpyrrole compounds, upon initial intramolecular arylation, undergo in situ removal of the protecting group to afford C(2)-functionalised derivatives. Although in present form the method is not without restrictions, it provides straightforward access to important derivatives of pyrrole and indole under mild conditions in synthetically acceptable yields.
Infrared (IR) spectra were recorded on an IR Thermo Scientific NICOLET iS10 (4950) spectrophotometer. Melting points were determined using a Boetius PHMK 05 apparatus without correction. 1H and 13C nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Ascend 400 (400 MHz) spectrometer. Deuterochloroform was used as a solvent, and chemical shifts are given in parts per million (δ) downfield from tetramethylsilane as the internal standard. Mass spectral data were recorded using an Orbitrap XL. Flash chromatography used a silica gel 60 (230–400 mesh), while thin-layer chromatography (TLC) was carried out using alumina plates with a 0.25 mm silica layer (Kieselgel 60 F254; Merck). Compounds were visualised by staining with potassium permanganate solution. The starting compounds 6, 12a and 12b were synthesised from pyrrole and appropriate o-iodo-aroylchloride following the literature procedure.[6]
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N-(2-Iodobenzoyl)pyrrole (6)
Flash chromatography (SiO2, 3:1 v/v PE–Et2O) afforded the product as a white, amorphous solid in 76% yield (225 mg from 1 mmol of starting pyrrole).
1H NMR (400 MHz, CDCl3): δ = 7.93 (d, J = 8.0 Hz, 1 H), 7.51–7.43 (m, 1 H), 7.39 (dd, J = 7.6, 1.4 Hz, 1 H), 7.28–7.19 (m, 1 H), 7.10 (bs, 2 H), 6.34 (bs, 2 H).
13C NMR (101 MHz, CDCl3): δ = 167.5, 140.2, 139.6, 131.8, 128.5, 128.0, 120.8, 114.2, 92.7.
The spectral data are consistent with those reported in the literature.[23]
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N-(2-Iodo-4-nitrobenzoyl)pyrrole (12a)
Flash chromatography (SiO2, 3:1 v/v PE–Et2O) afforded the product as a white solid in 45% yield (153 mg from 1 mmol of starting pyrrole); mp 129–130 °C.
IR (ATR): 2923, 1697, 1519, 1334, 729 cm−1.
1H NMR (400 MHz, CDCl3): δ = 8.23 (d, J = 2.6 Hz, 1 H), 8.16 (d, J = 8.7 Hz, 1 H), 8.05 (dd, J = 8.7, 2.5 Hz, 1 H), 7.07 (s, 2 H), 6.46–6.27 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 165.1, 147.8, 141.6, 141.1, 125.8, 123.1, 120.4, 114.3, 100.3.
HRMS (ESI, Q-TOF): m/z calcd for [C11H7IN2O3 + H–NO2 + Na+]: 319.95428; found: 320.25620.
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N-(3-Iodo-2-naphthoyl)pyrrole (12b)
Flash chromatography (SiO2, 3:1 v/v PE–Et2O) afforded the product as a beige solid in 37% yield (128 mg from 1 mmol of starting pyrrole); mp 120–121 °C.
IR (ATR): 3419, 2922, 1623, 1545, 695 cm−1.
1H NMR (400 MHz, CDCl3): δ = 8.29 (s, 1 H), 7.74 (s, 1 H), 7.71–7.66 (m, 1 H), 7.66–7.60 (m, 1 H), 7.45 (ddd, J = 6.9, 5.6, 3.4 Hz, 2 H), 7.02 (s, 2 H), 6.28–6.16 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 167.2, 139.2, 136.2, 135.2, 131.4, 128.5, 128.5, 128.3, 127.7, 126.8, 120.8, 113.9, 88.0.
HRMS (ESI, Q-TOF): m/z calcd for [C15H10INO + Na+]: 369.96993; found: 369.96962.
The starting compounds 12c and 14 were synthesised from indole or indole derivatives and o-iodo-benzoic acid following the literature procedure.[24]
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N-(2-Iodobenzoyl)indole (12c)
Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product as a white, amorphous solid in 50% yield (173 mg from 1 mmol of starting pyrrole).
1H NMR (400 MHz, CDCl3): δ = 8.39 (s, 1 H), 7.88 (d, J = 8.0 Hz, 1 H), 7.55 (d, J = 7.6 Hz, 1 H), 7.44 (t, J = 7.5 Hz, 1 H), 7.40–7.33 (m, 2 H), 7.29 (t, J = 7.4 Hz, 1 H), 7.18 (td, J = 7.8, 1.5 Hz, 1 H), 6.90 (s, 1 H), 6.57 (d, J = 3.7 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 167.9, 140.9, 139.4, 135.4, 131.5, 131.0, 128.2, 128.2, 126.6, 125.2, 124.3, 120.9, 116.4, 109.7, 92.4.
The spectral data are consistent with those reported in the literature.[25]
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2-tert-Butoxycarbonylamino-3-[1-(2-iodobenzoyl)-1H-indol-3-yl]propionic Acid Methyl Ester (14)
Flash chromatography (SiO2, 1:1 v/v PE–Et2O) afforded the product as a white solid in 43% yield (236 mg from 1 mmol of starting tryptophan derivative); mp 117–118 °C.
IR (ATR): 3339, 2972, 1739, 1676, 1149, 749 cm−1.
1H NMR (400 MHz, CDCl3): δ = 8.40 (s, 1 H), 7.94 (d, J = 7.9 Hz, 1 H), 7.51 (t, J = 7.6 Hz, 2 H), 7.45–7.31 (m, 3 H), 7.24 (td, J = 7.8, 1.6 Hz, 1 H), 6.72 (s, 1 H), 5.14 (d, J = 7.0 Hz, 1 H), 4.60 (d, J = 6.5 Hz, 1 H), 3.61 (s, 3 H), 3.31–2.98 (m, 2 H), 1.40 (s, 9 H).
13C NMR (101 MHz, CDCl3): δ = 172.0, 167.7, 154.9, 141.0, 139.5, 135.6, 131.6, 131.2, 128.3, 128.3, 125.6, 124.8, 124.3, 119.0, 117.8, 92.4, 89.7, 79.9, 79.5, 53.4, 52.3, 28.3.
HRMS (ESI, Q-TOF): m/z calcd for [C24H25N2O5 + Na+]: 571.07004; found: 571.06990.
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2-Arylpyrroles; General Procedure
The mixture of N-acylpyrrole or N-acylindole (0.10 mmol, 1 equiv), amine (0.3 mmol, 3 equiv), K3PO4 (0.15 mmol, 1.5 equiv), Pd(OAc)2 (0.01 mmol, 0.1 equiv) and PPh3 (0.02 mmol, 0.2 equiv) in MeCN (5 mL) was heated under a nitrogen atmosphere at reflux for 18 h. After completion of the reaction, the mixture was cooled to r.t., and the solvent was removed under reduced pressure. The crude mixture was purified by flash chromatography to afford the product.
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Morpholin-4-yl[2-(1H-pyrrol-2-yl)phenyl]methanone (7)
Compound 7 was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (16.4 mg, 64%) as a beige solid; mp 162–163 °C.
IR (ATR): 3185, 2924, 1599, 1107, 723 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.20 (s, 1 H), 7.54 (d, J = 7.8 Hz, 1 H), 7.44–7.34 (m, 1 H), 7.30–7.20 (m, 2 H), 6.95–6.77 (m, 1 H), 6.41 (t, J = 3.6 Hz, 1 H), 6.27 (dd, J = 5.9, 2.7 Hz, 1 H), 4.05 (dd, J = 12.9, 2.3 Hz, 1 H), 3.77–3.67 (m, 1 H), 3.51–3.33 (m, 3 H), 3.17–3.05 (m, 1 H), 3.00–2.89 (m, 1 H), 2.78 (ddd, J = 11.4, 8.6, 2.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 171.3, 132.6, 130.4, 130.3, 129.5, 128.1, 126.5, 126.4, 119.3, 109.6, 108.3, 66.6, 66.2, 47.6, 42.3.
HRMS (ESI, Q-TOF): m/z calcd for [C15H16N2O2 + H+]: 257.12845; found: 257.12842.
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Pyrrolo[2,1-a]isoindol-5-one (8)
Compound 8 was synthesised following the general procedure, omitting the amine. Flash chromatography (SiO2, 9:1 v/v PE–Et2O) afforded the product (16.7 mg, 99%) as a yellow solid; mp 62–63 °C.
1H NMR (400 MHz, CDCl3): δ = 7.55 (d, J = 7.2 Hz, 1 H), 7.34 (t, J = 7.2 Hz, 1 H), 7.19 (d, J = 7.2 Hz, 1 H), 7.09 (t, J = 7.0 Hz, 1 H), 6.93 (s, 1 H), 6.10 (d, J = 12.7 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 163.0, 136.4, 135.6, 134.4, 132.1, 127.1, 125.8, 119.5, 117.1, 116.6, 107.3.
The spectral data are consistent with those reported in the literature.[26]
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N-Hexyl-2-(1H-pyrrol-2-yl)benzamide (13a)
Compound 13a was synthesised following the general procedure. Flash chromatography (SiO2, 1:1 v/v PE–Et2O) afforded the product (16.5 mg, 61%) as a brown, amorphous solid.
IR (ATR): 3273, 2929, 1615, 1485, 762 cm−1.
1H NMR (400 MHz, CDCl3): δ = 10.21 (s, 1 H), 7.65–7.58 (m, 1 H), 7.45–7.38 (m, 2 H), 7.23 (td, J = 7.6, 1.0 Hz, 1 H), 6.90–6.80 (m, 1 H), 6.48 (t, J = 3.6 Hz, 1 H), 6.27 (dd, J = 5.9, 2.6 Hz, 1 H), 5.85 (s, 1 H), 3.36 (dd, J = 13.1, 7.0 Hz, 2 H), 1.54–1.46 (m, 2 H), 1.30 (d, J = 9.9 Hz, 6 H), 0.89 (t, J = 6.6 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 172.0, 133.5, 131.2, 130.7, 130.2, 128.9, 127.8, 125.9, 119.3, 109.1, 108.3, 40.2, 31.4, 29.3, 26.5, 22.5, 13.9.
HRMS (ESI, Q-TOF): m/z calcd for [C17H22N2O + Na+]: 293.16243; found: 293.16223.
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N-Benzyl-2-(1H-pyrrol-2-yl)benzamide (13b)
Compound 13b was synthesised following the general procedure. Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product (17.1 mg, 62%) as a beige solid; mp 109–110 °C.
IR (ATR): 3418, 3216, 1624, 1548, 761, 695 cm−1.
1H NMR (400 MHz, CDCl3): δ = 10.10 (s, 1 H), 7.60 (d, J = 7.8 Hz, 1 H), 7.41 (dd, J = 7.6, 2.1 Hz, 2 H), 7.29 (d, J = 7.4 Hz, 3 H), 7.19 (d, J = 7.6 Hz, 3 H), 6.81 (s, 1 H), 6.46 (s, 1 H), 6.26 (d, J = 2.8 Hz, 1 H), 6.14 (s, 1 H), 4.53 (d, J = 5.7 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 171.8, 137.3, 133.1, 131.2, 130.5, 130.3, 129.0, 128.8, 127.8, 127.7, 127.6, 126.0, 119.4, 109.1, 108.6, 44.2.
HRMS (ESI, Q-TOF): m/z calcd for [C18H16N2O + Na+]: 299.11548; found: 299.11539
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N-(1-Phenylethyl)-2-(1H-pyrrol-2-yl)benzamide (13c)
Compound 13c was synthesised following the general procedure. Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product (18.6 mg, 64%) as a brown oil.
IR (ATR): 3278, 1633, 1516, 757, 726 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.96 (s, 1 H), 7.61 (d, J = 7.8 Hz, 1 H), 7.42 (dd, J = 14.0, 7.5 Hz, 2 H), 7.31 (dd, J = 15.6, 8.1 Hz, 2 H), 7.26–7.21 (m, 4 H), 6.78 (d, J = 1.3 Hz, 1 H), 6.47 (s, 1 H), 6.26 (d, J = 3.0 Hz, 1 H), 6.08 (d, J = 6.7 Hz, 1 H), 5.20 (d, J = 7.1 Hz, 1 H), 1.48 (d, J = 6.9 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 170.9, 142.5, 133.3, 131.2, 130.5, 130.3, 129.0, 128.7, 127.9, 127.4, 126.0, 126.1, 119.4, 109.1, 108.5, 49.6, 21.7.
HRMS (ESI, Q-TOF): m/z calcd for [C19H18N2O + H+]: 291.14919; found: 291.14909.
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N-Phenethyl-2-(1H-pyrrol-2-yl)benzamide (13d)
Compound 13d was synthesised following the general procedure. Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product (19.7 mg, 68%) as a brown oil.
IR (ATR): 3291, 2925, 1634, 1524, 727, 698 cm−1.
1H NMR (400 MHz, CDCl3): δ = 10.17 (s, 1 H), 7.61 (d, J = 7.9 Hz, 1 H), 7.39 (t, J = 7.6 Hz, 1 H), 7.31–7.14 (m, 5 H), 7.08 (d, J = 7.1 Hz, 2 H), 6.86 (s, 1 H), 6.48 (s, 1 H), 6.28 (d, J = 2.9 Hz, 1 H), 5.83 (s, 1 H), 3.65 (q, J = 6.6 Hz, 2 H), 2.84 (t, J = 6.8 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 172.1, 138.4, 133.4, 130.2, 128.9, 128.7, 128.6, 127.6, 126.6, 125.9, 119.3, 109.2, 108.5, 41.3, 35.3.
HRMS (ESI, Q-TOF): m/z calcd for [C19H18N2O + H+]: 291.14919; found: 291.14908.
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N-Allyl-2-(1H-pyrrol-2-yl)benzamide (13e)
Compound 13e was synthesised following the general procedure. Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product (10.8 mg, 48%) as a brown, amorphous solid.
IR (ATR): 3268, 3089, 1651, 1597, 760, 718 cm−1.
1H NMR (400 MHz, CDCl3): δ = 10.14 (s, 1 H), 7.63 (d, J = 7.9 Hz, 1 H), 7.42 (t, J = 8.0 Hz, 2 H), 7.31–7.12 (m, 1 H), 6.85 (d, J = 1.5 Hz, 1 H), 6.48 (s, 1 H), 6.26 (d, J = 2.6 Hz, 1 H), 5.98–5.67 (m, 2 H), 5.23–5.06 (m, 2 H), 4.05–3.88 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 171.9, 133.3, 133.2, 131.3, 130.6, 130.3, 129.0, 127.8, 126.0, 119.4, 117.0, 109.1, 108.5, 42.6.
HRMS (ESI, Q-TOF): m/z calcd for [C14H14N2O + H+]: 227.11789; found: 227.11784.
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Pyrrolidin-1-yl[2-(1H-pyrrol-2-yl)phenyl]methanone (13f)
Compound 13f was synthesised following the general procedure. Flash chromatography (SiO2, 2:1 v/v PE–Et2O) afforded the product (15.3 mg, 64%) as a light-brown solid; mp 146–147 °C.
IR (ATR): 3159, 2978, 1587, 1438, 758, 688 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.72 (s, 1 H), 7.59 (d, J = 8.0 Hz, 1 H), 7.41–7.32 (m, 1 H), 7.29–7.17 (m, 2 H), 6.82 (d, J = 1.5 Hz, 1 H), 6.45 (d, J = 3.6 Hz, 1 H), 6.24 (dd, J = 5.9, 2.6 Hz, 1 H), 3.59 (t, J = 6.6 Hz, 2 H), 3.02 (s, 2 H), 1.85 (dd, J = 13.7, 6.8 Hz, 2 H), 1.71 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ = 171.2, 133.8, 130.8, 130.0, 129.3, 128.3, 126.7, 126.1, 119.3, 109.1, 107.8, 48.6, 45.76, 25.7, 24.4.
HRMS (ESI, Q-TOF): m/z calcd for [C15H16N2O + H+]: 241.13354; found: 241.13353.
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N-(2-Hydroxyethyl)-2-(1H-pyrrol-2-yl)benzamide (13g)
Compound 13g was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (9.4 mg, 41%) as a brown oil.
IR (ATR): 3253, 2922, 1615, 1068, 756, 696 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.89 (s, 1 H), 7.54 (d, J = 7.7 Hz, 1 H), 7.44 (t, J = 7.0 Hz, 1 H), 7.40 (td, J = 7.7, 1.1 Hz, 1 H), 7.22 (t, J = 7.5 Hz, 1 H), 6.88 (d, J = 1.4 Hz, 1 H), 6.43 (s, 1 H), 6.27 (dd, J = 5.7, 2.6 Hz, 1 H), 6.21 (s, 1 H), 3.68–3.54 (m, 2 H), 3.45 (dd, J = 10.2, 5.5 Hz, 2 H).
13C NMR (101 MHz, CDCl3): δ = 172.2, 133.5, 132.1, 131.2, 130.5, 130.4, 129.3, 128.6, 128.5, 128.1, 126.5, 119.5, 109.2, 108.5, 61.8, 42.5.
HRMS (ESI, Q-TOF): m/z calcd for [C13H14N2O2 + Na+]: 253.09475; found: 253.09445.
#
(2-(1H-Pyrrol-2-yl)phenyl)(3H-spiro[benzofuran-2,4′-piperidin]-1′-yl)methanone (13h)
Compound 13h was synthesised following the general procedure. Flash chromatography (SiO2, 1:2 v/v PE–Et2O) afforded the product (27.2 mg, 76%) as a brown, amorphous solid.
IR (ATR): 3389, 2917, 1612, 1042, 731 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.38 (s, 1 H), 7.55 (d, J = 7.9 Hz, 1 H), 7.43–7.36 (m, 1 H), 7.33–7.19 (m, 4 H), 7.18–7.09 (m, 1 H), 6.95 (d, J = 1.5 Hz, 1 H), 6.84 (dd, J = 4.6, 3.6 Hz, 1 H), 6.44 (s, 1 H), 6.40 (dd, J = 5.9, 2.7 Hz, 1 H), 5.00 (dt, J = 20.8, 10.3 Hz, 2 H), 4.85–4.74 (m, 1 H), 3.39–3.07 (m, 3 H), 1.69 (dd, J = 13.5, 2.2 Hz, 1 H), 1.58 (dd, J = 13.2, 4.7 Hz, 1 H), 1.35–1.27 (m, 1 H), 0.95–0.78 (m, 1 H).
13C NMR (101 MHz, CDCl3): δ = 171.3, 144.5, 138.5, 133.7, 131.1, 129.9, 129.1, 128.2, 127.8, 127.3, 126.7, 126.1, 121.1, 121.0, 119.0, 109.7, 108.4, 84.5, 70.8, 44.5, 39.1, 36.5, 36.1.
HRMS (ESI, Q-TOF): m/z calcd for [C23H22N2O2 + H+]: 359.1754; found: 359.17553
#
(2-Oxa-5-azabicyclo[2.2.1]hept-5-yl)-[2-(1H-pyrrol-2-yl)phenyl]methanone (13i)
Compound 13i was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (16.1 mg, 60%) as a white solid; mp 176–177 °C.
IR (ATR): 3189, 2960, 1567, 1448, 804, 719 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.43–9.32 (m, 1 H, rotamers a and b), 7.56 (t, J = 8.3 Hz, 1 H, rotamers a and b), 7.50–7.34 (m, 1 H, rotamers a and b), 7.27 (dd, J = 11.8, 5.9 Hz, 2 H, rotamers a and b), 6.94–6.72 (m, 1 H, rotamers a and b), 6.43 (s, 1 H, rotamers a and b), 6.25 (dd, J = 5.8, 2.9 Hz, 1 H, rotamers a and b), 5.07 (s, 0.4 H, rotamer b), 4.60 (s, 0.6 H, rotamer a), 4.41 (s, 0.4 H, rotamer b), 3.88 (s, 0.6 H, rotamer a), 3.78 (s, 1 H, rotamers a and b), 3.68–3.43 (m, 1.6 H, rotamers a and b), 3.34 (s, 0.4 H, rotamer b), 3.01–2.90 (m, 0.6 H, rotamer a), 2.62 (s, 0.4 H, rotamer b), 1.85–1.76 (m, 1 H, rotamers a and b), 1.59 (s, 0.6 H, rotamer a), 1.10 (s, 0.4 H, rotamer b).
13C NMR (101 MHz, CDCl3): δ = 170.9, 132.9, 130.3, 130.1, 129.6, 129.6, 128.3, 128.2, 126.5, 126.4, 119.3, 109.5, 108.2, 108.2, 76.0, 73.7, 59.8, 56.3, 55.9, 35.7.
HRMS (ESI, Q-TOF): m/z calcd for [C16H16N2O2 + Na+]: 291.1104; found: 291.11026.
#
Morpholin-4-yl[4-nitro-2-(1H-pyrrol-2-yl)phenyl]methanone (13j)
Compound 13j was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (21.9 mg, 73%) as a brown, amorphous solid.
IR (ATR): 3196, 2850, 1621, 1515, 1336, 730 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.46 (s, 1 H), 8.24 (dd, J = 8.7, 2.4 Hz, 1 H), 8.12 (d, J = 2.3 Hz, 1 H), 7.70 (d, J = 8.7 Hz, 1 H), 7.04–6.90 (m, 1 H), 6.71–6.57 (m, 1 H), 6.40–6.26 (m, 1 H), 4.08 (d, J = 12.4 Hz, 1 H), 3.88–3.72 (m, 1 H), 3.59–3.40 (m, 3 H), 3.19 (ddd, J = 13.2, 8.4, 3.1 Hz, 1 H), 2.95 (dd, J = 13.4, 3.5 Hz, 1 H), 2.85 (td, J = 8.5, 4.2 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 169.2, 145.3, 136.4, 132.2, 128.6, 128.4, 124.5, 122.4, 121.9, 111.5, 110.8, 66.5, 47.8, 42.6.
HRMS (ESI, Q-TOF): m/z calcd for [C15H15N3O4 + H-NO2 + Na+]: 279.10985; found: 279.09341.
#
Morpholin-4-yl-[3-(1H-pyrrol-2-yl)naphthalen-2-yl]methanone (13k)
Compound 13k was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (18.0 mg, 59%) as a grey solid; mp 199–200 °C.
IR (ATR): 3173, 2964, 1594, 1480, 1107, 727 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.21 (s, 1 H), 7.97 (s, 1 H), 7.82 (dd, J = 10.8, 8.3 Hz, 2 H), 7.73 (s, 1 H), 7.59–7.38 (m, 2 H), 6.89 (d, J = 1.2 Hz, 1 H), 6.51 (s, 1 H), 6.30 (dd, J = 5.6, 2.7 Hz, 1 H), 4.11 (d, J = 13.1 Hz, 1 H), 3.83–3.68 (m, 1 H), 3.55–3.32 (m, 3 H), 3.17–3.02 (m, 1 H), 3.03–2.88 (m, 1 H), 2.76 (ddd, J = 11.4, 8.8, 2.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 171.1, 133.6, 131.9, 131.5, 130.4, 127.9, 127.8, 127.8, 127.2, 126.7, 126.4, 125.9, 119.4, 109.7, 108.6, 66.6, 66.5, 47.6, 42.4.
HRMS (ESI, Q-TOF): m/z calcd for [C19H18N2O2 + Na+]: 329.12605; found: 329.12572.
#
[2-(1H-Indol-2-yl)phenyl]pyrrolidin-1-ylmethanone (13l)
Compound 13l was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (21.5 mg, 74%) as a white, amorphous solid.
IR (ATR): 3241, 2921, 1598, 1447, 747 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.58 (s, 1 H), 7.75 (d, J = 7.7 Hz, 1 H), 7.62 (d, J = 7.8 Hz, 1 H), 7.49–7.31 (m, 4 H), 7.18 (dd, J = 11.1, 4.0 Hz, 1 H), 7.11 (d, J = 7.1 Hz, 1 H), 6.75 (d, J = 1.3 Hz, 1 H), 3.59 (s, 2 H), 3.01 (s, 2 H), 1.87–1.72 (m, 2 H), 1.66 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ = 170.8, 136.9, 136.8, 135.2, 129.6, 129.4, 129.5, 128.4, 127.6, 126.8, 122.2, 120.4, 119.9, 111.4, 101.6, 48.6, 45.8, 25.7, 24.3.
HRMS (ESI, Q-TOF): m/z calcd for [C19H18N2O + H+]: 291.14919; found: 291.14911.
#
[2-(1H-Indol-2-yl)phenyl]morpholin-4-ylmethanone (13m)
Compound 13m was synthesised following the general procedure. Flash chromatography (SiO2, Et2O) afforded the product (23.2 mg, 76%) as a brown oil.
IR (ATR): 3185, 3131, 1599, 1470, 1010, 712 cm−1.
1H NMR (400 MHz, CDCl3): δ = 9.16 (s, 1 H), 7.70 (d, J = 7.8 Hz, 1 H), 7.63 (d, J = 7.8 Hz, 1 H), 7.46 (td, J = 7.7, 1.1 Hz, 1 H), 7.42–7.34 (m, 2 H), 7.30 (d, J = 7.5 Hz, 1 H), 7.20 (t, J = 7.5 Hz, 1 H), 7.12 (t, J = 7.4 Hz, 1 H), 6.72 (d, J = 1.2 Hz, 1 H), 4.03–3.92 (m, 1 H), 3.69–3.60 (m, 1 H), 3.58–3.46 (m, 1 H), 3.39–3.24 (m, 2 H), 3.10 (ddd, J = 13.1, 8.0, 3.0 Hz, 1 H), 2.98–2.89 (m, 1 H), 2.72 (ddd, J = 11.1, 8.0, 2.8 Hz, 1 H).
13C NMR (101 MHz, CDCl3): δ = 170.9, 136.8, 136.2, 133.5, 129.9, 129.6, 129.1, 128.3, 127.9, 126.6, 122.6, 120.6, 120.2, 111.2, 102.2, 66.5, 66.4, 47.4, 42.2.
HRMS (ESI, Q-TOF): m/z calcd for [C19H18N2O2 + H+]: 307.1441; found: 307.14402.
#
2-tert-Butoxycarbonylamino-3-(6-oxo-6H-isoindolo[2,1-a]indol-11-yl)propionic Acid Methyl Ester (15)
Compound 15 was synthesised following the general procedure. Flash chromatography (SiO2, 9:1 v/v PE–Et2O) afforded the product (36.9 mg, 88%) as a yellow, amorphous solid.
IR (ATR): 1716, 1686, 1364, 1164, 728 cm−1.
1H NMR (400 MHz, CDCl3): δ = 7.87 (d, J = 7.9 Hz, 1 H), 7.75 (d, J = 7.5 Hz, 1 H), 7.63 (d, J = 7.5 Hz, 1 H), 7.50 (t, J = 7.6 Hz, 1 H), 7.32 (ddd, J = 18.3, 17.0, 7.5 Hz, 3 H), 7.15 (t, J = 7.5 Hz, 1 H), 5.28 (d, J = 7.6 Hz, 1 H), 4.73 (d, J = 6.9 Hz, 1 H), 3.58 (s, 3 H), 3.38 (d, J = 6.4 Hz, 2 H), 1.40 (s, 9 H).
13C NMR (101 MHz, CDCl3): δ = 171.9, 162.3, 154.9, 139.5, 136.4, 134.8, 134.5, 133.9, 133.7, 133.5, 131.6, 129.1, 128.6, 128.4, 126.6, 125.3, 123.7, 121.5, 120.4, 80.1, 53.6, 52.6, 28.4, 28.2.
HRMS (ESI, Q-TOF): m/z calcd for [C24H24N2O5 + Na+]: 443.15774; found: 443.15814.
#
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-1758-6312.
- Supporting Information
-
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Corresponding Authors
Publication History
Received: 28 December 2021
Accepted after revision: 02 February 2022
Accepted Manuscript online:
02 February 2022
Article published online:
29 March 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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References
- 1a Rostami H, Shiri L. Appl. Organomet. Chem. 2021; 35: e6209
- 1b Hunjan MK, Panday S, Gupta A, Bhaumik J, Das P, Laha JK. Chem. Rec. 2021; 21: 715
- 1c Sarosh I, Hina R, Rabiya JA, Ramsha JA, Asma M, Mark GM. Curr. Org. Chem. 2020; 24: 1196
- 1d Apetrei R.-M, Camurlu P. J. Electrochem. Soc. 2020; 167: 037557
- 1e Li Petri G, Spanò V, Spatola R, Holl R, Raimondi MV, Barraja P, Montalbano A. Eur. J. Med. Chem. 2020; 208: 112783
- 1f Leonardi M, Estévez V, Villacampa M, Menéndez JC. Synthesis 2019; 51: 816
- 1g Ahmad S, Alam O, Naim MJ, Shaquiquzzaman M, Alam MM, Iqbal M. Eur. J. Med. Chem. 2018; 157: 527
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