Sodium Cyanide → 6-fluoro-3-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-fluoro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.100 g, 0.22 mmol), Pd(PPh3)4 (0.022 g, 0.24 mmol), sodium cyanide (0.014 g, 0.285 mmol), and CuI (0.004 g, 0.022 mmol) in acetonitrile (5 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate afforded 6-fluoro-3-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-4-carbonitrile (0.035 g, 45%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.32 (s, 2H), 4.80 (s, 2H), 7.20 (d, 2H), 7.37 (m, 3H), 7.49 (d, 1H). GC-MS: m/z 350 (M)+.

Provenance & Evidence