To a mixture of ethyl 3-(2-chloro-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-3-yl)propanoate (120 mg, 0.204 mmol), 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (80 mg, 0.306 mmol), cesium carbonate (133 mg, 0.408 mmol) and dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium (II) (13.3 mg, 0.02 mmol) was added 1,4-dioxane (1.86 mL) and H2O (0.186 mL). A steady stream of N2 was bubbled through the reaction mixture for 5 minutes then the mixture was heated to 90° C. for 9 h. The mixture was cooled to ambient temperature, diluted with EtOAc, and washed successively with H2O (1×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-100% EtOAc/Hexanes as eluent and further purified by silica gel column chromatography using a step gradient of 0-20-80% EtOAc/CH2Cl2 as eluent. MS (M+H)+: 687.
