Triphenylphosphine → 2-Chloro-11-fluoro-5-methyl-5,6-dihydroindolo[2,1-a][2,6]naphthyridine

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Reaction Steps

To a suspension of 2-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propan-1-ol (60 mg, 0.21 mmol) and DEAD (111 mg, 0.63 mmol) in THF (4 mL) was added PPh3 (156 mg, 0.63 mmol) at 0° C. under N2, and the mixture was stirred for 12 hours. Then the mixture was diluted with H2O and extracted with EA. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated to give 2-chloro-11-fluoro-5-methyl-5,6-dihydroindolo[2,1-a][2,6]naphthyridine (30 mg, yield: 56%). 1H-NMR (CDCl3, 400 MHz) δ 8.26 (s, 1H), 7.54 (s, 1H), 7.05˜7.15 (m, 3H), 6.73˜6.77 (m, 1H), 4.16˜4.20 (m, 1H), 4.00˜4.04 (m, 1H), 3.31˜3.35 (m, 1H), 1.30 (d, J=8.0 Hz, 3H). MS (M+H)+: 287/289.

Provenance & Evidence