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

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-(3,6-dihydro-2H-thiopyran-4-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.2 mmol), 11-fluoro-2-(trimethylstannyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (105 mg, 0.26 mmol) in 1,4-dioxane (5 mL) was added Pd(PPh3)4(10 mg) under nitrogen. The reaction mixture was heated at 100° C. overnight, concentrated in vacuo to remove 1,4-dioxane and purified by prep-TLC (PE:EA=1:1) to give 2-(3,6-dihydro-2H-thiopyran-4-yl)-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (15 mg, yield: 11%). 1H-NMR (CDCl3, 400 MHz) δ 7.97 (s, 1H), 7.58 (s, 1H), 7.47 (s, 2H), 7.18˜7.23 (m, 2H), 7.11 (d, J=8.4 Hz, 1H), 6.80˜6.86 (m, 2H), 6.05 (d, J=4.8 Hz, 1H), 5.99 (s, 2H), 3.41 (t, J=2.0 Hz, 2H), 3.35 (s, 3H), 3.00 (d, J=4.8 Hz, 3H), 2.90 (t, J=5.6 Hz, 2H), 2.80 (d, J=3.2 Hz, 2H), 2.71 (s, 3H). MS (M+H)+: 619.

Provenance & Evidence