Isopropyl iodide → ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 82186

Reaction equation

HRID 82186 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([F:13])([F:14])[F:12])=[N:9][N:8]([CH:22]([CH3:24])[CH3:23])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 596095Ethyl 3-(Trifluoromethyl)pyrazole-4-carboxylate

Product 1

HCID 57574507ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (13 g, 62.5 mmol) and cesium carbonate (61.1 g, 187.5 mmol) in DMF (70 mL) was added 2-iodo-propane (6.86 mL, 68.75 mmol) and the resulting mixture allowed to stir at room temperature for 16 hours. The crude reaction mixture was poured onto water (100 mL) and extracted with EtOAc (100 mL×3). The combined organics were washed with water (50 mL×2), brine (50 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid in 65% yield, 10.2 g.

Workup

  1. customThe crude reaction mixture
  2. additionwas poured onto water (100 mL)
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organics were washed with water (50 mL×2), brine (50 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db3f9af732d44991838e63257ff6b3ca
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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