To a mixture of ethyl 3-(2,6-dichloropyridin-3-yl)propanoate (170 mg, 0.685 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (344 mg, 0.685 mmol), XantPhos Biphenyl precatalyst (60.9 mg, 0.069 mmol), and cesium carbonate (670 mg, 2.056 mmol) was added 1,4-dioxane (5.7 mL) and H2O (1.2 mL). A steady stream of N2 was bubbled through the reaction mixture for 5 minutes then the mixture was heated to 70° C. for 16 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. 1H NMR δ (ppm) (CHCl3-d): 8.01˜7.96 (3H, m), 7.75 (1H, t, J=7.74 Hz), 7.69 (1H, s), 7.55 (1H, d, J=7.70 Hz), 7.27˜7.21 (2H, m) 5.91 (1H, br s), 4.19 (2H, q, J=7.12 Hz), 3.27˜3.20 (3H, m), 3.18˜3.12 (2H, m), 3.03 (3H, d, J=4.92 Hz), 2.90˜2.80 (3H, m), 2.77 (2H, t, J=7.51 Hz), 1.30 (3H, t, J=7.15 Hz). MS (M+H)+: 588.
