To a mixture of 5-(6-chloro-5-(3-hydroxypropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (180 mg, 0.330 mmol), 4-fluoroindole-2-boronic acid pinacol ester (129 mg, 0.494 mmol), cesium carbonate (215 mg, 0.659 mmol) and dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium (II) (21.49 mg, 0.033 mmol) was added 1,4-dioxane (3 mL) and H2O (0.3 mL). A steady stream of N2 was bubbled through the reaction mixture for 5 minutes then the mixture was heated to 90° C. for 3 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/CH2Cl2 as eluent. The residue was triturated with CH2Cl2 to provide the title compound as a white solid. 1H NMR δ (ppm) (CHCl3-d): 10.30 (1H, br s), 8.07 (1H, s), 8.00 (2H, dd, J=8.56, 5.31 Hz), 7.78 (1H, d, J=7.88 Hz), 7.69 (1H, s), 7.50 (1H, d, J=7.85 Hz), 7.27˜7.23 (3H, m), 7.17˜7.13 (2H, m), 6.81˜6.78 (1H, m), 5.93˜5.87 (1H, m), 3.89 (2H, d, J=5.37 Hz), 3.24 (2H, t, J=7.86 Hz), 3.16 (3H, s), 3.02 (3H, d, J=4.90 Hz), 2.92 (3H, s), 2.13 (2H, t, J=7.43 Hz). MS (M+H)+: 645.
