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

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 3-bromo-1-(4-methylphenyl)-1H-indazole-6-carboxylate (0.30 g, 0.87 mmol), 2-chlorophenylboronic acid (0.21 g, 1.34 mmol), cesium carbonate (0.86 g, 2.64 mmol), copper(I) chloride (91.6 mg, 0.93 mmol), 1,1′-bis(diphenylphosphino)ferrocene (51.6 mg, 0.09 mmol) and palladium(II) acetate (9.8 mg, 0.04 mmol) under argon was added N,N-dimethylformamide (4.3 mL). The mixture stirred in a sealed tube at 90° C. for 30 min. The mixture was cooled to ambient temperature and quenched with saturated sodium bicarbonate (15 mL). The mixture was extracted with ethyl acetate (3×15 mL). The combined organic layers were 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 (0.25 g): LC-MS [M+1]=377.2.

Provenance & Evidence