Water → 7-Amino-2-phenylimidazo[1,2-A]pyridine-6-carbonitrile

Participants

Reaction Steps

2-Bromoacetophenone (1.11 g, 5.6 mmol) and NaHCO3 (470 mg) were added to a solution of 3-cyano-4,6-diaminopyridine (500 mg, 3.7 mmol) in methanol (7.5 ml), and the mixture was heated to reflux overnight. Upon cooling, water (4 ml) was added and the precipitate was filtered and dried under vacuum to give a first crop of the desired product. The filtrate was evaporated, the residue was taken up in ethyl acetate (20 ml) and washed (water, brine). The organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50) to give a second crop of the desired product. The combined crops gave the title compound (350 mg, 40%). MS (m/e)=235.1 [M+H+].

Provenance & Evidence