3-Aminobenzonitrile → N-(3-cyanophenyl)-4-methyl-1,2,5-oxadiazole-3-carboxamide

Participants

Reaction Steps

4-Methyl-1,2,5-oxadiazole-3-carboxylic acid (200 mg, 1.6 mmol) and bromotris-(pyrrolydino)phosphonium hexafluorophosphate was dissolved in a 1/1 mixture of DMF/DCM. To the mixture was added DMAP (120 mg, 0.95 mmol) and 3-amino-benzonitrile (184 mg, 1.6 mol) followed by N,N-diisopropylethylamine. The reaction mixture was stirred at rt overnight. The volatiles were removed in vacuo and the residue dissolved with chloroform and loaded onto a 40 g Silica ISCO cartridge eluting with 25%-50% EtOAc/Hexane to afford a white powder (25 mg). MF=C11H8N4O2; LCMS calculated for C11H9N4O2(M+H)+: m/z=229.1.

Provenance & Evidence