Potassium Carbonate → HCID 25070420, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-Bromo-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (375 mg; 0.96 mmol; 1 eq) in a mixture of 1,2-dimethoxyethane and water (3.4 mL/1.4 mL), 3-acetamidophenylboronic acid (242 mg, 1.35 mmol; 1.4 eq) is added under argon followed by potassium carbonate (266 mg; 1.93 mmol; 2 eq) and tetrakis(triphenylphosphine)palladium (89 mg; 0.08 mmol; 0.08 eq). The solution is allowed to stir for 17 hours at 90° C. until the reaction is complete on TLC. The crude mixture is cooled to room temperature, diluted with ethyl acetate (15 mL) and washed with water (10 mL). The resulting organic phase is dried over sodium sulfate, filtered and concentrated under vacuum to afford a grey powder. This solid is passed through two successive columns (eluent column 1: ethyl acetate 100%; eluent column 2: methylene chloride/methanol 9:1) to afford the title compound as an off-white powder (256 mg; 0.58 mmol; 60%).

Provenance & Evidence