Potassium Carbonate → 3-chloro-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine

HRID 887700Notes

Reaction equation

HRID 887700 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.Cl[C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][C:16]1[C:11]([N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 179762913-chloro-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridineYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

3-Trifluoromethyl-1H-pyrazole (15.30 g), 2,3-dichloro-pyridine (16.64 g) and potassium carbonate (26.42 g) were suspended in dry DMF (100 mL) and stirred for 3 h at 130° C., overnight at rt and again for 11 h at 130° C. After complete consumption of the starting material, the reaction was cooled to room temperature and quenched with water. The mixture was extracted 2× with ethyl acetate, the combined org. layers were washed 2× with water, brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, hexane/ethyl acetate=8:1, then 5:1, Rf=0.35 in hexane/ethyl acetate=3:1) to afford 22.88 g of the title compound of the formula

Workup

  1. customAfter complete consumption of the starting material
  2. temperaturethe reaction was cooled to room temperature
  3. customquenched with water
  4. extractionThe mixture was extracted 2× with ethyl acetate
  5. washlayers were washed 2× with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by column chromatography (silica gel 60, hexane/ethyl acetate=8:1

Sources & evidence

ORD record
ord-3f5062989b984ac19454ba36cbcb4b25
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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