Pyridine → 1-(4-methoxyphenyl)-5-[4-(1H-pyrrol-1yl)phenyl]-3-(trifluoro methyl)-1H-1,2,4-triazole

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Reaction Steps

To a suspension of 4-(1H-pyrrol-1yl)benzoic acid (337 mg, 1.8 mmol) in dichloromethane (3.5 mL), oxalyl chloride (0.157 mL, 1.8 mmol) and then dimethylformamide (10 microL) were added. The mixture was stirred overnight. The solvent was removed under reduced pressure. Pyridine (0.146 mL, 1.8 mmol) and a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (350 mg, 1.5 mmol) in 3.5 mL of dioxane were added to a suspension of the acyl chloride in 3.5 mL of dioxane. The mixture was refluxed with stirring for 3 hours. After cooling, the solvent was removed under reduced pressure and 0.1 N hydrochloric acid and dichloromethane were added to the residue. The organic layer was separated and the aqueous layer was extracted with dichloromethane. A combined layer was washed with 0.1 N hydrochloric acid and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The desired product was purified by silica gel column chromatography (hexane-ethyl acetate 8:1-5:1) to give 1-(4-methoxyphenyl)-5-[4-(1H-pyrrol-1yl)phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole (74 mg, 12.8% yield)

Provenance & Evidence