Sodium Carbonate → 2-(4-(difluoromethyl)phenyl)-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 degassed solution of 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (120 mg, 0.22 mmol), 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (64 mg, 0.22 mmol), Na2CO3 (62 mg, 0.45 mmol), in 1,4-dioxane (3 mL) and H2O (0.1 mL) was added Pd2(dba)3 (5 mg) and X-Phos (5 mg) under N2. Then the mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled to RT and filtered. The filtrate was washed with H2O and dried over Na2SO4. After concentrated, the residue was purified by prep-HPLC to give the product (30 mg, yield: 21%). 1H-NMR (CDCl3, 400 MHz) δ 8.08 (d, J=8.0 Hz, 2H), 8.03 (s, 1H), 7.74˜7.64 (m, 4H), 7.47 (d, J=7.6 Hz, 1H), 7.30 (s, 1H), 7.22˜7.14 (m, 2H), 6.89˜6.81 (m, 1H), 6.81˜6.73 (m, 1H), 6.00 (d, J=4.4 Hz, 1H), 4.37 (t, J=6.4 Hz, 2H), 3.40 (s, 3H), 3.34 (t, J=6.4 Hz, 2H), 3.02 (d, J=4.8 Hz, 3H), 2.72 (s, 3H). MS (M+H)+: 645.

Provenance & Evidence