Potassium Cyanide → 2-(2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)acetonitrile

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Reaction Conditions

Reaction Steps

A mixture of (2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methyl methanesulfonate (1 g, 2.52 mmol) and KCN (491 mg, 7.55 mmol) in DMF (15 mL) was stirred at 80° C. for 15 hours. The mixture was diluted with water (30 mL) and extracted with EA (20 mL×3). The organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated. The residue was purified by column (PE:EA=1:1) to afford the desired product of 2-(2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)acetonitrile (600 mg, yield: 73%). 1H-NMR (CDCl3, 400 MHz) δ 7.49 (d, J=8.0 Hz, 1H), 7.35 (s, 1H), 7.18 (d, J=8.0 Hz 2H), 7.09 (d, J=8.4 Hz, 1H), 6.77˜6.79 (m, 1H), 5.00˜5.06 (m, 1H), 3.48˜3.54 (m, 1H), 3.27 (d, J=16.4 Hz, 1H), 2.54˜2.59 (m, 1H), 2.37˜2.44 (m, 1H). MS (M+H)+: 312/314.

Provenance & Evidence