Bromoacetonitrile → 9-Benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide

Participants

Reaction Steps

To a stirred solution of 9-benzyl-5-hydroxy-7-methoxycarbazole-4-carboxamide (0.75 g, 2.17 mmol) in DMF (76 ml) and THF (16 ml) and added 60% NaH (0.11 g, 2.71 mmol). After 15 min bromoacetonitrile (0.20 ml, 2.93 mmol) was added and the reaction was allowed to stir for 4 h. The reaction was diluted with EtOAc, extracted with water, then brine, dried (Na2SO4), and chromatographed on silica gel using a CH2Cl2-EtOAc-methanol gradient to give the titled compound (0.52 g, 63%). MS (ES+) 386

Provenance & Evidence