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Synfacts 2007(5): 0479-0479  
DOI: 10.1055/s-2007-968469
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

3-Amino-Imidazopyridines by a Microwave-Assisted Synthesis

Contributor(s): Victor Snieckus, Oluwole Familoni
E. F. DiMauro*, J. M. Kennedy
Amgen Inc., Cambridge, USA
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Publikationsdatum:
24. April 2007 (online)

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Significance

A microwave-assisted, Pd-catalyzed four-component synthesis of 3-amino imidazopyridines in a one-pot process is reported. In the initial process, a three-component Ugi reaction of a 2-aminopyridine with an aldehyde and an isonitrile leads to a 3-amino imidazole. The subsequent Pd-catalyzed Suzuki coupling in the same pot is possible due to the compatibility of the boronate with the mild Lewis acid conditions. An attempt to perform the reaction not in this sequence but by carrying out the Suzuki coupling before cyclization was not feasible. Paraformaldehyde was used as part of a three-component Ugi reaction for the first time.