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

HRID 251907Notes

Reaction equation

HRID 251907 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)C=O>O>[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

6

Reactant 4

HCID 6228DimethylformamideHCID 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 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 15.30 g of 3-trifluoromethyl-1H-pyrazole, 16.64 g of 2,3-dichloropyridine, 26.42 g of potassium carbonate and 100 ml of N,N-dimethylformamide was stirred at 130° C. for 14 hours. The reaction mixture was allowed to cool to room temperature and then water was poured thereto. The mixture was extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 22.88 g of 3-chloro-2-(3-trifluoromethyl-1H-pyrazol-1-yl)pyridine of the formula:

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate two times
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c542371070984076bfee99b6db5600c9
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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