To a mixture of 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.200 g, 0.502 mmol) in tetrahydrofuran (5 mL) was added 0.50 M (3-fluorophenyl)(iodo)zinc in tetrahydrofuran (1.20 mL, 0.602 mmol) with stirring, followed by addition of tetrakis(triphenylphosphine)palladium(0) (29.0 mg, 0.0251 mmol). The reaction mixture was heated at 60° C. overnight. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The crude mixture was purified on silica gel, eluting with 0 to 60% EtOAc in hexane, to give the desired product (154 mg, 89%). LCMS calculated for C18H15ClFN2O2(M+H)+: m/z=345.1; found: 345.0.
