Potassium Carbonate → 5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (60 mg, 0.13 mmol), 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (42 mg, 0.15 mmol) and K2CO3 (26 mg, 0.19 mmol) in 1,4-dioxane (1 mL) and water (0.01 mL) were added X-Phos (10 mg) and Pd2(dba)3 (10 mg) under nitrogen. The mixture was heated at 110° C. for 3 hours and filtered through the celite pad. The filtrate was extracted with EtOAc and the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by prep-HPLC to give 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (30 mg, yield: 40%). 1H-NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 8.03 (s, 1H), 7.73 (s, 1H), 7.68 (s, 1H), 7.52 (s, 2H), 7.20˜7.25 (m, 3H), 7.12 (d, J=8.4 Hz, 1H), 6.84˜6.88 (m, 1H), 6.02 (s, 2H), 5.93 (d, J=4.8 Hz, 1H), 3.35 (s, 3H), 3.02 (d, J=4.8 Hz, 3H), 2.78 (s, 3H). MS (M+H)+: 587.

Provenance & Evidence