Cesium carbonate → 5-chloro-3-methyl-1-(2-methylprop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3) (1.852 g, 8.16 mmol) and cesium carbonate (7.97 g, 24.47 mmol) were added to a round bottom flask and suspended in NMP (25 mL) under nitrogen. 3-bromo-2-methylprop-1-ene (1.101 g, 8.16 mmol) was added to the suspension and then refluxed at 90° C. overnight. 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 tan solid 5-chloro-3-methyl-1-(2-methylprop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (74-1). MS (M+H)+: observed=238.59, calculated=238.69.

Provenance & Evidence