Sodium Carbonate → HCID 25120173, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-bromo-7-trifluoromethoxy-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (300 mg; 0.74 mmol; 1 eq) in N,N-dimethylformamide (8 mL), pyrazoleboronic acid (166 mg, 1.48 mmol; 2 eq) is added under argon followed by sodium carbonate (314 mg; 2.96 mmol; 4 eq) and tetrakis(triphenylphosphine)palladium (257 mg; 0.22 mmol; 0.3 eq). The solution is allowed to stir for 17 hours at 130° C. until the reaction is complete on TLC. The crude mixture is cooled to room temperature, diluted with ethyl acetate (50 mL), washed once with a saturated solution of sodium hydrogenocarbonate (90 mL) and three times with brine (3×25 mL). The resulting organic phase is dried over sodium sulfate, filtered and concentrated under vacuum to afford a crude brown powder. This solid is purified by chromatography on silica gel (gradient dichloromethane/methanol 98:2→95:5) to afford the title compound as an orange powder. Recristallization of this solid from ethyl acetate at 0-5° C. afforded the pure title compound (88 mg; 0.22 mmol; 30%) after filtration, washing with diethyl ether and drying of the resulting beige powder.

Provenance & Evidence