Sodium Cyanide → 7-methyl-1-oxo-2-(4-chloro-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 5-bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.205 g, 0.59 mmol), Pd(PPh3)4 (0.070 g, 0.06 mmol), sodium cyanide (0.038 g, 0.8 mmol), and CuI (0.013 g, 0.07 mmol) in acetonitrile (3 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate (typically 2:1 hexane-EtOAc) afforded 7-methyl-1-oxo-2-(4-chloro-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (0.93 g, 54%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.78 (s, 3H), 4.26 (s, 2H), 4.65 (s, 2H), 7.24 (d, 2H), 7.33 (d, 2H), 7.52 (d, 2H). GC-MS: m/z 296 (M)+, 261 (M−35)+.

Provenance & Evidence