Dimethylformamide → 5-chloro-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

6-Chloro-N2-methylpyridine-2,3-diamine (1-2, 35 g, 222 mmol) and 1,1′-carbonyldiimidazole (63 g, 389 mmol) were added to a round bottom flask and suspended in DMF (150 mL). The solution was heated to 80° C. in an oil bath overnight. The reaction was then suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine(×5), dried over sodium sulfate, filtered, and concentrated to produce 5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3) as a white solid. HRMS (M+H)+: observed=184.0279, calculated=184.0272.

Provenance & Evidence