Potassium Hydroxide → 2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine

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Reaction Conditions

Reaction Steps

A mixture of 2-(6-chloro-3-vinylpyridin-2-yl)-4-fluoro-1H-indole (1.0 g, 3.7 mmol), DMSO (2.5 mL), TBAC (0.3 mL, 50% aq. solution) and KOH (10 mL, 60% a.q. solution) was stirred under N2 at 100° C. for 4 h. After cooled to RT and extracted with CH2Cl2, the organic layer was washed with water, brine, dried over Na2SO4 and concentrated on a rotary evaporator. The residue was purified by column chromatography (PE:EA=100:1˜10:1) to give the product of 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (0.5 g, yield: 50%). And 150 mg of un-reacted 2-(6-chloro-3-vinylpyridin-2-yl)-4-fluoro-1H-indole was recycled during the column purification. 1H-NMR (CDCl3, 400 MHz) δ 7.50 (d, J=7.8 Hz, 1H), 7.38 (s, 1H), 7.22˜7.04 (m, 3H), 6.86˜6.71 (m, 1H), 4.27 (t, J=6.8 Hz, 2H), 3.22 (t, J=6.8 Hz, 2H). MS (M+H)+: 273.

Provenance & Evidence