2-[4-(1,3,4-Oxadiazol-2-yl)phenyl]acetonitrile → 3-(2-Fluoro-4-trifluoromethyl-phenyl)-5-(4-[1,3,4]oxadiazol-2-yl-phenyl)-3H-[1,2,3]triazol-4-ylamine

Participants

Reaction Steps

To a stirred and ice-cooled solution of sodium methoxide (0.158 g, 2.9252 mmol) in methanol (25 ml), commercial 2-[4-(1,3,4-oxadiazol-2-yl)phenyl]acetonitrile (0.430 g, 2.3401 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.400 g, 1.9501 mmol) are added under a nitrogen atmosphere. The reaction mixture is kept at 0° C. for 1 h, and then allowed to attain spontaneously room temperature overnight. The reaction mixture is concentrated, added water (30 ml), and extracted with ethylacetate (3×100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a pink solid (0.74 g, 97% mass balance). The crude residue is purified by column chromatography over silica gel (230-400 mesh), eluting with 50% ethylacetate in petroleum ether, to obtain the title compound as a yellow solid (0.280 g, 37% yield). M.p. 184.6-186.1° C. LC-ESI-HRMS of [M+H]+ shows 391.0927 Da. Calc. 391.093046 Da, dev. −0.9 ppm.

Provenance & Evidence