3-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazole → 2-Butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-6-phenyl-3H-imidazo[1,2-b][1,2,4]triazole

Participants

Reaction Steps

A mixture of 212 mg (0.640 mmole) of 3-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazole (from Example 1, Step D), 151 mg (0.757 mmol) of α-bromophenylacetaldehyde [T. L. Jacobs and W. R. Scott, Jr., J. Am. Chem. Soc., 75, 5500 (1953)], and 2.0 ml of absolute ethanol was stirred at reflux under N2 for 6 hours. The mixture was cooled and concentrated in vacuo. The residue was chromatographed on a column of silica gel (27×2.5 cm) packed in CH2Cl2 (elution with 1% and then 4% MeOH in CH2Cl2). Concentration of the appropriate pooled product fractions afforded 65.3 mg (24%) of the title compound as a yellow oil; homogeneous by TLC in 19:1 CH2Cl2 -MeOH.

Provenance & Evidence