Triethylamine → N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl-methyl)-3-methyl-1H-indole-2-carboxamide

Participants

Reaction Steps

3-Methylindole-2-carboxylic acid (0.5 g) and 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate (2.1 g) was dissolved in DMF (42 ml). Triethylamine (1.6 ml) and Bop reagent (1.32 g) were added under ice-cooling, and the mixture was stirred for 6 hours. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous citric acid solution, saturated brine, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and methanol as an eluent and recrystallized from a mixed solvent of ethyl acetate and hexane to give 0.22 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl-methyl)-3-methyl-1H-indole-2-carboxamide.

Provenance & Evidence