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

Participants

Reaction Conditions

Reaction Steps

Methyl 3-bromo-1-(4-methylphenyl)-1H-indazole-6-carboxylate 173.7 mg, 0.503 mmol), 2,6-difluorophenylboronic acid, pinacol ester (183.4 mg, 0.764 mmol), Cs2CO3 (505.1 mg, 1.550 mmol), copper(I) chloride (52.7 mg, 0.532 mmol), 1,1′-bisdiphenylphosphino ferrocene (29.3 mg, 0.053 mmol), and palladium(II) acetate (6.5 mg, 0.029 mmol) were placed in a 10-20 mL microwave vial under Ar. N,N-dimethylformamide (2.50 mL) was added and the vessel sealed. The reaction mixture was heated to 90° C. and allowed to stir for 30 min. The reaction was stopped, quenched by addition of saturated aqueous ammonium chloride (15 mL), and extracted with ethyl acetate (3×15 mL). The combined organic phases were washed with saturated aqueous ammonium chloride (1×15 mL), saturated aqueous sodium chloride (1×10 mL), dried (sodium sulfate), and concentrated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 24 g column) on a CombiFlash purification system eluting with ethyl acetate-hexanes (0-10%). The title compound (102.1 mg, 0.270 mmol, 53.6% yield) was recovered as a white solid. LC-MS: [M+1]=379.2.

Provenance & Evidence