To a solution of methyl 4-amino-3-bromo-5-nitrobenzoate (1.0 g, 3.64 mmol), (4-fluorophenyl)-boronic acid (0.76 g, 5.45 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (0.18 g, 0.27 mmol), palladium(II) acetate (20.0 mg, 0.09 mmol) and diisopropylamine (0.52 mL, 3.64 mmol) were added N,N-dimethylformamide (13.6 mL) and water (4.5 mL). The mixture was heated to 80° C. After 1 h, the mixture was cooled to ambient temperature and ethyl acetate was added. The organic layer was dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (0.93 g): LC-MS [M+1]=291.2.
