Toluene → HCID 178441893, compound

Participants

Reaction Steps

A mixture of 95.0 mg (0.213 mmol) of 2-butyl-3-[(2'-cyanobiphenyl-4-yl)methyl]-6-methyl-5-phenyl-3H-imidazo[1,2-b][1,2,4]triazole (from Step F), 158 mg (0.769 mmol) of trimethyltin azide, and 2.0 ml of toluene was stirred at reflux under N2 for 24 hours. The mixture was concentrated in vacuo, and the residue was treated with 3 ml of dry MeOH and 1.0 g of silica gel. The resulting mixture was stirred at room temperature in a stoppered flask overnight. The solvent was removed by rotary evaporation in vacuo to give a dry powder, which was added as a slurry in CH2Cl2 to the top of a column of silica gel (26×2.5 cm) packed in CH2Cl2. Gradient elution of the column with 1.5% MeOH in CH2Cl2 and concentration of the product fractions yielded 40.4 mg (37%) of the title compound as a yellow gum, which, upon trituration with ether, was transformed to a tan solid (28 mg, 25%), mp 207°-208° C.; homogeneous by TLC in 90:10:0.1 CH2Cl2 -MeOH-AcOH.

Provenance & Evidence