5-(6-(4-fluoro-1H-indol-2-yl)-5-(4-hydroxybut-1-en-1-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-(11-fluoro-6-(2-hydroxyethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Steps

A solution of (Z and E)-5-(6-(4-fluoro-1H-indol-2-yl)-5-(4-hydroxybut-1-en-1-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (300 mg, 0.457 mmol) in DMAc (9 mL) was added K3PO4.3H2O (606 mg, 2.28 mmol) under N2. It was put into a pre-heated oil-bath at 110° C. for 3 hours. The mixture was diluted with H2O and it was extracted with EtOAc (500 mL×5). The combined organic phase was washed with brine, and dried over Na2SO4. The crude product was purified with Prep-HPLC to give the pure product of 5-(11-fluoro-6-(2-hydroxyethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, yield: 30%). 1H-NMR (CDCl3, 400 MHz) δ 7.97 (s, 1H), 7.88˜7.92 (m, 2H), 7.63 (s, 1H), 7.60 (s, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.09˜7.22 (m, 5H), 6.72 (t, J=8.4 Hz, 1H), 5.83 (s, 1H), 5.02 (d, J=6.4 Hz, 1H), 3.43˜3.55 (m, 4H), 3.35 (s, 3H), 3.10 (d, J=24.0 Hz, 1H), 2.94 (d, J=4.4 Hz, 3H), 2.61 (s, 3H), 1.78 (d, J=5.2 Hz, 2H). MS (M+H)+: 657.

Provenance & Evidence