8-Hydroxyquinoline → 3-(1H-1,2,4-triazol-1-yl)-5-(trifluoromethyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-5-(trifluoromethyl)pyridin-2-amine (5.0 g), 1,2,4-triazole (1.44 g), copper(I) iodide (0.496 g), 8-quinolinol (0.378 g), potassium carbonate (2.88 g) and DMSO (50 mL) was stirred at 120° C. for 7 hr under nitrogen gas atmosphere. The reaction solution was allowed to be cooled to room temperature, diluted with ethyl acetate, and filtered through basic silica gel column (ethyl acetate). The filtrate was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified successively by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (2.4 g).

Provenance & Evidence