Carbonate Ion → Methyl 3-(2-chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 3-bromo-1-isopropyl-1H-indazole-6-carboxylate (0.32 g, 1.08 mmol), 2-chlorophenylboronic acid (0.51 g, 3.29 mmol), cessium carbonate (1.15 g, 3.52 mmol), copper(I) chloride (0.11 g, 1.09 mmol), 1,1′-bis(diphenylphosphino)ferrocene (61.1 mg, 0.11 mmol) and palladium(II) acetate (12.6 mg, 0.06 mmol) under argon was added N,N-dimethylformamide (4.3 mL). The mixture was stirred in a sealed tube at 90° C. for 18 h. After 18 h, the mixture was cooled to ambient temperature and quenched with saturated aqueous sodium bicarbonate (15 mL). The mixture was extracted with ethyl acetate (3×15 mL). The combined organic layer was washed with saturated aqueous ammonium chloride (4×10 mL), saturated aqueous sodium chloride (1×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (100% hexanes→85% hexanes/ethyl acetate) gave the title compound (0.11 g): LC-MS [M+1]=329.2.

Provenance & Evidence