Dimethylformamide → Methyl 4-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 4-bromo-1-methyl-1H-indole-6-carboxylate (0.45 g, 1.69 mmol), (4-fluorophenyl)-boronic acid (0.36 g, 2.53 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (81.0 mg, 0.13 mmol), palladium(II) acetate (9.5 mg, 0.04 mmol) and diisopropylamine (0.60 mL, 4.22 mmol) were added N,N-dimethylformamide (6.3 mL) and water (2.1 mL). The mixture was heated to 80° C. for 1 h. The mixture was cooled to ambient temperature and ethyl acetate was added. The organic layer was washed with water (3×10 mL), saturated aqueous sodium chloride (1×10 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (0.41 g): LC-MS [M+1]=284.1.

Provenance & Evidence