Synthesis 2016; 48(23): 4269-4277
DOI: 10.1055/s-0035-1561489
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of Imidazo[1,5-a]pyridine-1-carboxylic Acids

Dmytro O. Tverdiy*
a   Department of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine   Email: tverdiy_d@ukr.net
b   Department of Organic Chemistry, National Technical University of Ukraine ‘Kiev Polytechnic Institute’, 37 Peremohy Ave., 03056, Kiev, Ukraine
c   Azepine Ltd., Suite 7777, 6 Slington House, Rankine Road, Basingstoke, RG24 8PH, UK
,
Maksym O. Chekanov
a   Department of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine   Email: tverdiy_d@ukr.net
,
Pavlo V. Savitskiy
a   Department of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine   Email: tverdiy_d@ukr.net
,
Anatolii R. Syniugin
a   Department of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine   Email: tverdiy_d@ukr.net
,
Sergiy M. Yarmoliuk
a   Department of Medicinal Chemistry, The Institute of Molecular Biology and Genetics NAS of Ukraine, 150 Zabolotnogo Str., 03143, Kiev, Ukraine   Email: tverdiy_d@ukr.net
,
Andrey A. Fokin
b   Department of Organic Chemistry, National Technical University of Ukraine ‘Kiev Polytechnic Institute’, 37 Peremohy Ave., 03056, Kiev, Ukraine
› Author Affiliations
Further Information

Publication History

Received: 30 March 2016

Accepted after revision: 31 May 2016

Publication Date:
27 July 2016 (online)


Abstract

We report a novel and efficient approach to the synthesis of imidazo[1,5-a]pyridine-1-carboxylic acids. By using the reaction of 2-(aminomethyl)pyridine with acyl chlorides followed by one-pot treatment with trifluoroacetic anhydride, 2,2,2-trifluoro-1-imidazo[1,5-a]pyridin-1-ylethanones were obtained, which were then converted into imidazo[1,5-a]pyridine-1-carboxylic acids in high preparative yields through haloform cleavage.

Supporting Information

Primary Data