Potassium Carbonate → HCID 86707229, compound

HRID 2408238Notes

Reaction equation

HRID 2408238 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[I:9].[F:10][C:11]([F:18])([F:17])[C:12]1[CH:16]=[CH:15][NH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:14]2[CH:15]=[CH:16][C:12]([C:11]([F:18])([F:17])[F:10])=[N:13]2)[CH:5]=[CH:4][C:3]=1[I:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 27365592-Chloro-4-fluoro-1-iodobenzene

Product 1

HCID 86707229HCID 86707229, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 2-chloro-4-fluoro-1-iodo-benzene (3.6 g, 14.3 mmol) and 3-trifluoromethyl-1H-pyrazole (1.9 g, 14.4 mmol) in N,N-dimethylformamide (40 mL) was added potassium carbonate (2.4 g, 17.2 mmol), and the resulting mixture was heated at 135° C. for 12 h. The reaction mixture was cooled to room temperature, poured in cold water (80 mL) and extracted with dichloromethane (2×40 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with 10% ethyl acetate in hexanes to afford the title compound (4.2 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane (2×40 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluted with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4c3bd4e8d5394922a8ff5abf4c11c299
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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