Reaction Steps
A mixture of 2-chloro-11-fluoro-6-(2-(3-fluoroazetidin-1-yl)ethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (100 mg, 0.269 mmol), N-methyl-6-(N-methylmethylsulfonamido)-2-(6-methylpyridin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (150 mg, 0.295 mmol), K2CO3 (75 mg, 0.537 mmol), Pd2(dba)3 (15 mg, 0.027 mmol) and X-Phos (10 mg, 0.054 mmol) in dioxane/H2O (4 mL/10 d) was stirred at 110° C. for 4 hours under N2 atmosphere. The mixture was then filtered through Celite and concentrated. The residue was purified by column chromatography (PE:EA=2:1) to afford the desired product of 5-(11-fluoro-6-(2-(3-fluoroazetidin-1-yl)ethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)-2-(6-methylpyridin-3-yl)benzofuran-3-carboxamide (85 mg, yield: 44.9%). 1H-NMR (CDCl3, 400 MHz) δ 8.97 (s, 1H), 8.17 (t, J=6.0, 2.0 Hz, 1H), 8.00 (s, 1H), 7.61 (t, J=8.0 Hz, 2H), 7.39 (d, J=8.0 Hz, 1H), 7.24 (d, J=6.8 Hz, 2H), 7.12 (s, 2H), 6.73˜6.77 (m, 1H), 5.97 (d, J=4.8 Hz, 1H), 4.97˜5.14 (m, 1H), 4.95 (d, J=6.0 Hz, 1H), 3.49˜3.56 (m, 4H), 3.33 (s, 3H), 3.00˜3.06 (m, 3H), 2.95 (d, J=4.8 Hz, 3H), 2.62 (s, 3H), 2.58 (s, 3H), 2.33˜2.36 (m, 1H), 1.59˜1.56 (m, 2H). MS (M+H)+: 711.
