Aniline → 6-(dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Participants

Reaction Steps

0.46 ml of a 2M solution of trimethylaluminum in toluene is added dropwise to a solution, cooled to 0° C., of 60.8 μl of aniline in 3 ml of toluene, followed, at 20° C., by the addition of 76 mg of ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate. The reaction mixture is stirred at ambient temperature for 15 minutes. It is cooled to 0° C. and then 20 ml of a saturated ammonium chloride solution are added. The organic phase is dried over magnesium sulfate, filtered through Celite and evaporated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, elution being carried out with a mixture of dichloromethane and ethyl acetate. The fractions comprising the product are combined and concentrated to dryness under reduced pressure. The residue obtained is crystallized from methanol to give 36 mg of 6-(dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a gray powder.

Provenance & Evidence