Cesium carbonate → HCID 88057427, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3, 516 mg, 2.81 mmol) and cesium carbonate (4.97 g, 15.26 mmol) were added to a round bottom flask and suspended in NMP (4.6 mL) under nitrogen. 1,1-Difluoro-2-(iodomethyl)cyclopropane (481 μL, 5.06 mmol) was added to the suspension and then heated to 100° C. in microwave reactor for 10 min. Following this duration, the reaction was cooled to room temperature and suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine(×5), dried over sodium sulfate, filtered, and concentrated. The mixture was purified using reverse-phase chromatography (5-95% 0.1% TFA in H2O:acetonitrile) to give 5-chloro-1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (6-1) as an off-white solid. MS m/z (M+H): calculated=274.0553; observed=274.0551.

Provenance & Evidence