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

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 2-chloro-11-fluoro-5,6-dihydroindolo[2,1-a][2,6]naphthyridine (70 mg, 0.26 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (155 mg, 0.31 mmol) and K2CO3 (53 mg, 0.38 mmol) in 1,4-dioxane (2 mL) and water (0.05 mL) were added X-Phos (10 mg) and Pd2(dba)3 (10 mg) under nitrogen. The mixture was heated at 120° C. for 3 hours and filtered through the celite pad. The filtrate was extracted with EtOAc, then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by prep-HPLC to give the desired compound (50 mg, yield: 30%). 1H-NMR (CDCl3, 400 MHz) δ 8.54 (s, 1H), 7.91˜7.98 (m, 4H), 7.62 (s, 1H), 7.09˜7.16 (m, 5H), 6.74 (t, J=8.8 Hz, 1H), 5.95 (s, 1H), 4.29 (t, J=6.0 Hz, 2H), 3.23 (t, J=6.0 Hz, 2H), 3.17 (s, 3H), 2.95 (d, J=4.0 Hz, 3H), 2.83 (s, 3H). MS (M+H)+: 613.

Provenance & Evidence