Cesium carbonate → Methyl 3-(2-chlorophenyl)-1-(4-methylphenyl)-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-[3-bromo-1-(4-methylphenyl)-1H-indol-6-yl]ethanone (0.11 g, 0.31 mmol), 2-chlorophenylboronic acid (73.9 mg, 0.47 mmol), cesium carbonate (0.31 g, 0.94 mmol), copper(I) chloride (32.8 mg, 0.33 mmol), 1,1′-bis(diphenylphosphino)ferrocene (18.6 mg, 34.0 μmol) and palladium(II) acetate (3.5 mg, 16.0 μmol) under Ar was added N,N-dimethylformamide (4.3 mL). The mixture was stirred in a sealed tube at 90° C. for 30 min. The mixture was cooled to ambient temperature and quenched with saturated aqueous sodium bicarbonate (1×15 mL). The mixture was extracted with ethyl acetate (3×15 mL). The combined organic layer was washed with saturated aqueous sodium chloride (1×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (100% hexanes→95% hexanes/ethyl acetate) gave the title compound (0.11 g): LC-MS [M+1]=376.0.

Provenance & Evidence