Cesium carbonate → (E)-5-(6-chloro-5-(2-ethoxyvinyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of (E)-6-bromo-2-chloro-3-(2-ethoxyvinyl)pyridine (3.37 g, 12.84 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (6.45 g, 12.84 mmol), cesium carbonate (10.46 g, 32.1 mmol), and 1,1′ Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.524 g, 0.642 mmol) was added 1,4-Dioxane (83 mL) followed by H2O (8.34 mL). A steady stream of N2 was bubbled through the reaction mixture for 7 minutes then the mixture was heated to 60° 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 solid residue was triturated with EtOAc and further purified by silica gel column chromatography using a gradient of 0-30% EtOAc/CH2Cl2 as eluent. Further purification by silica gel column chromatography with a gradient of 0-100% EtOAc/Hexanes as eluent provided the title compound as a tan solid. 1H NMR δ (ppm) (CHCl3-d): 8.03˜7.97 (3H, m), 7.79 (1H, d, J=7.96 Hz), 7.69 (1H, s), 7.52 (1H, d, J=7.50 Hz), 7.28˜7.00 (2H, m), 7.11 (1H, d, J=13.00 Hz), 6.12 (1H, d, J=13.00 Hz), 5.91 (1H, br s), 4.04 (2H, q, J=7.04 Hz), 3.24 (3H, s), 3.03 (3H, d, J=4.87 Hz), 2.89 (3H, s), 1.44 (3H, t, J=7.00). MS (M+H): 557.

Provenance & Evidence