Dimethyl Sulfoxide → HCID 68681541, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [5-bromo-1-(2,2,2-trifluoro-ethyl)-1H-indol-2-yl]-morpholin-4-yl-methanone (1.49 g, 4 mmol), palladium acetate (171 mg, 0.76 mmol), 1,3-bis(diphenylphosphino)propane (346 mg, 0.84 mmol), triethylamine (0.58 mL, 4 mmol), ethanol (3 mL) and dimethylsulfoxide (3 mL) was flushed with carbon monoxide. The reaction mixture was stirred vigorously at 75° C. (oil bath), under carbon monoxide (1 Atm) for 19 h. The red mixture was diluted with ethyl acetate, filtered and partitioned between ethyl acetate and brine. The organic layer was washed with brine and dried in vacuo. The crude product was purified by flash chromatography on silica gel with dichloromethane:ethyl acetate (98:2 v/v) as eluant, to give 924 mg (63%) of the desired compound as an off-white solid.

Provenance & Evidence