Ethyl Acetate → 5-chloro-1-[(2,2-difluoro-1-methylcyclopropyl)methyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

5-chloro-3-methyl-1-(2-methylprop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (74-1) (6 g, 25.2 mmol) was added to a round bottom flask along with chloro(difluoro)acetic acid-sodium (1:1) (38.42 g, 252 mmol) this was mixed together with a spatula then heated to 200° C. for one hour. The reaction was then 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 normal phase chromatography (0-60% Ethyl Acetate/Hexanes), and the desired fractions were collected to produce the solid 5-chloro-1-[(2,2-difluoro-1-methylcyclopropyl)methyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (74-2). HRMS (M+H)+: observed=288.0713, calculated=288.0715.

Provenance & Evidence