5-bromo-2-(4-fluorophenyl)-N-methyl-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxamide → 5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 11-fluoro-2-(trimethylstannyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (60 mg, 0.14 mmol), 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxamide (50 mg, 0.11 mmol) in DMF (4 mL), Pd(PPh3)4 was added. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was filtered through a Celit pad. The filtrate was concentrated in vacuo. The resulting residue was suspended in water, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-HPLC to provide 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxamide (20 mg, yield: 29.2%). 1H-NMR (CDCl3, 400 MHz) δ 7.97 (s, 1H), 7.89˜7.93 (m, 2H), 7.44 (s, 1H), 7.40˜7.42 (m, 2H), 7.11˜7.19 (m, 4H), 7.05 (d, J=8.8 Hz, 1H), 6.77˜6.82 (m, 1H), 5.92 (s, 2H), 5.85 (br s, 1H), 3.83 (t, J=7.2 Hz, 2H), 2.95 (d, J=4.8 Hz, 3H), 2.26 (t, J=8.4 Hz, 2H), 2.00˜2.06 (m, 2H). MS (M+H)+: 591.

Provenance & Evidence