To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.049 mmol), 4-chloro-2-(4-chloropyridin-2-yl)-5,7-difluoro-3-methylquinoline (0.10 g, 0.31 mmol), vinyl boronic acid MIDA ester (0.056 g, 0.31 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.1 mL) was added sodium tert-butoxide (0.074 g, 0.77 mmol). The reaction mixture was heated to 100° C. and stirring continued for 76 h. The crude product was purified by column chromatography on silica gel (0 to 50% hexanes/EtOAc) to give the desired product 4-chloro-5,7-difluoro-3-methyl-2-(4-vinylpyridin-2-yl)quinoline. Mass Spectrum (ESI) m/e=317.0 (M+1).
