Reaction #792210

Reaction equation

water

3-(1H-1,2,4-triazol-3-yl)pyridine

2-chloro-6-(trifluoromethyl)pyridine

potassium carbonate

→

2-[3-(Pyridin-3-yl)-1H-1,2,4-triazol-1-yl]-6-(trifluoromethyl)pyridine

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Extractionthe mixture was extracted three times with ethyl acetate
3. 3
   WashThe organic phases were washed with saturated sodium chloride solution
4. 4
   Dryingdried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

100 mg (684 μmol) of 3-(1H-1,2,4-triazol-3-yl)pyridine (preparation cf. J. Org. Chem. 1979, 44, 4160-4164), 124 mg (683 μmol) of 2-chloro-6-(trifluoromethyl)pyridine and 142 mg (1.03 mmol) of potassium carbonate were initially charged in 5 ml of N,N-dimethylformamide, and the mixture was stirred at 120° C. for about 18 hours. After cooling, water was added and the mixture was extracted three times with ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. This gave 180 mg (90% of theory) of 2-[3-(pyridin-3-yl)-1H-1,2,4-triazol-1-yl]-6-(trifluoromethyl)pyridine as a white solid.

Source