Water → HCID 67517286, compound

HRID 705028Notes

Reaction equation

HRID 705028 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:2]1.Cl[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]2[N:4]=[CH:5][N:1]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]=3)[N:2]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6023342-Chloro-6-(trifluoromethyl)pyridineHCID 178420775HCID 178420775, compound

Product 1

HCID 67517286HCID 67517286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

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.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34548fed80004ad1b8ce75e31245c770
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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