Potassium Carbonate → 3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

Participants

Reaction Steps

To a mixture of 3-fluoro-4-nitropyridine-N-oxide (3.46 g) and tert-butyl 4-aminopiperidine-1-carboxylate (2.745 g) in acetonitrile (150 ml) was added anhydrous potassium carbonate (2.74 g) and the resulting mixture was refluxed for 8 hours. The mixture was filtered and washed well with dichloromethane. The organics were concentrated to dryness and the residue was purified by column chromatography eluting with a mixture of ethyl acetate and dichloromethane (1:1) to give the titled compound as a yellow solid. Yield 3.25 g. NMR (d6 DMSO) 1.4 (s, 9H), 1.5 (M, 2H), 1.9 (m, 2H), 2.95 (m, 2H), 3.9 (m, 3H), 7.5 (dd, 1H), 7.85 (d, 1H), 8.05 (d, 1H) 8.4 (d, 1H).

Provenance & Evidence