Cesium carbonate → HCID 66661228, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-bromo-1-(4-methylphenyl)-1H-indazole-5-carboxylate (150.3 mg, 0.435 mmol), 2-chlorophenylboronic acid, pinacol ester (210.4 mg, 0.882 mmol), palladium(II) acetate (5.2 mg, 0.023 mmol), copper(I) chloride (88.5 mg, 0.894 mmol), cesium carbonate (431.8 mg, 1.325 mmol), and 1,1′-bisdiphenylphosphino ferrocene (26.4 mg, 0.048 mmol) were dissolved in N,N-dimethylformamide (2200 μl) at 25° C. under Ar. The reaction mixture was warmed to 100° C. and allowed to stir for 3 h. The reaction was stopped, cooled to room temperature, quenched by addition of saturated aqueous ammonium chloride (10 mL), and extracted with ethyl acetate (3×10 mL). The combined organic phases washed with saturated aqueous ammonium chloride (2×10 mL) and saturated aqueous sodium chloride (1×10 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. Crude product purified by flash chromatography (RediSep SiO2, 24 g column) on a CombiFlash Rf purification system eluting with ethyl acetate-hexanes (0-30%). The title compound (117.4 mg, 0.312 mmol, 71.6% yield) was recovered as a light yellow/white solid. LC-MS: [M+1]=377.1.

Provenance & Evidence