Potassium Hydroxide → 2-Chloro-10-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(6-chloro-3-vinylpyridin-2-yl)-5-fluoro-1H-indole (100 mg, 0.36 mmol), DMSO (0.5 mL), TBAC (0.1 mL of 50% a.q. solution) and KOH (1.0 mL of 60% a.q. solution) was stirred under N2 at 100° C. for 4 h. After cooled and extracted with EtOAc, the organic layer was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by prep-TLC (PE:EA=10:1) to give the product of 2-chloro-10-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (50 mg, yield: 50.0%). 1H-NMR (CDCl3, 400 MHz) δ 7.51 (d, J=8.0 Hz, 1H), 7.25˜7.38 (m, 3H), 7.15 (d, J=8.0 Hz, 1H), 6.98˜7.04 (m, 1H), 4.26 (d, J=6.4 Hz, 2H), 3.22 (d, J=6.4 Hz, 2H). MS (M+H)+: 273/275.

Provenance & Evidence