Potassium Carbonate → HCID 86654734, compound

Participants

Reaction Conditions

Reaction Steps

To an oven dry flask was added tert-butyl (1S,2R)-2-(7-bromo-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (40 mg, 0.075 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (20.99 μL, 0.151 mmol), and potassium carbonate (31.3 mg, 0.226 mmol) in dioxane (1959 μL) and water (196 μL). The resulting tan solution was degassed with nitrogen for 5 min. Palladium chloride (dppf) (5.52 mg, 7.54 mmol) was added and the mixture was degassed for an additional 2 min. The vessel was capped and the reaction mixture was heated at 100° C. with stirring overnight. The reaction mixture was cooled to RT, diluted with EtOAc (5 mL), and washed with water (5 mL) and brine (5 mL). The organic layer was collected, dried over Na2SO4 and concentrated to give the title compound as a brown viscous oil, which was used without purification (45 mg). [M+H] calc'd for C26H35N5O3, 466. found, 466.

Provenance & Evidence