Potassium Carbonate → 2-(2,4-difluorophenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2,4-difluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (500 mg, 0.96 mmol), 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (240 mg, 0.87 mmol) and K2CO3. (241 mg, 1.75 mmol) in 1,4-dioxane (5 mL) and H2O (5 drop) were added X-Phos (10 mg) and Pd2(dba)3 (10 mg) under N2. The reaction mixture was stirred at 100° C. for 10 hours and concentrated in vacuo to remove 1,4-dioxane. The reaction mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to give the product (230 mg, yield: 42%). 1H-NMR (CDCl3, 400 MHz) δ 8.08 (s, 1H), 7.7˜57.81 (m, 1H), 7.66˜7.69 (m, 2H), 7.46 (d, J=8.0 Hz, 1H), 7.28 (s, 1H), 7.15˜7.18 (m, 2H), 6.98˜7.09 (m, 2H), 6.79 (t, J=8.4 Hz, 1H), 5.81 (br s, 1H), 4.35 (t, J=6.4 Hz, 2H), 3.39 (s, 3H), 3.32 (t, J=6.4 Hz, 2H), 2.96 (d, J=4.8 Hz, 3H), 2.68 (s, 3H). MS (M+H)+: 631.

Provenance & Evidence