Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C–N bond forming reactions with enolizable heterocycles

In this Letter we report a rapid and facile access to C2-substituted imidazo[4,5-b]pyridine analogues utilizing palladium mediated Buchwald–Hartwig cross-coupling reactions. The use of enolizable heterocycles as cross-coupling partners resulted in a wide range of imidazo[4,5-b]pyridine analogues which are prone to have medicinal relevance. Xantphos and Pd(OAc)2 were found to be more effective for the coupling of 2-halo imidazo[4,5-b]pyridines with pyridone nucleophiles. A regioselective approach for the synthesis of 2-substituted 3H-imidazo[4,5-b]pyridine and 1H-imidazo[4,5-b]pyridine is also reported.