3-Amino-4-[N-(4-cyanophenyl)amino]pyridine → 4-(2-Methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzonitrile

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Reaction Steps

A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (9.31 g, 4.3 mmol), triethyl-orthoacetate (40 ml) and acetic anhydride (30 ml) was heated at reflux for 2 hours under nitrogen, cooled, then concentrated under reduced pressure. The brown residue was dissolved in 1 M bydrochloric acid and washed with ethyl acetate (200 ml). The aqueous layer was rendered basic with saturated aqueous ammonia and extracted with dichloromethane (3×200 ml). The combined extracts were washed with water, dried (MGSO4) and concentrated to give 1-(4-cyanophenyl)-2-methylimidazor4,5-c]pyridine, 6.5 g, as a brown solid.

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