Cesium carbonate → HCID 54760300, compound

Participants

Reaction Conditions

Reaction Steps

5-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4) (35 mg, 0.138 mmol), 2-cyanophenylboronic acid pinacol ester (79 mg, 0.345 mmol), cesium carbonate (135 mg, 0.414 mmol), and bis(tri-t-butylphosphine)palladium(0) (7 mg, 0.014 mmol) were added to a microwave vial, and purged with nitrogen. Dioxane (1.1 ml) and water (0.3 ml) were added and the suspension was heated at 90° C. overnight. The reaction was cooled to room temperature, diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-[1-(cyclopropylmethyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzonitrile (1-5). HRMS (M+H)+: observed=305.1403, calculated=305.1397.

Provenance & Evidence