Potassium Carbonate → Ethyl 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1890768Notes

Reaction equation

HRID 1890768 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]([F:20])([F:19])[C:9]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][NH:11][N:10]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>CC(C)=O>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:11]2[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:8]([F:7])([F:19])[F:20])=[N:10]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 178469923HCID 178469923, compound

Product 1

HCID 58243468Ethyl 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add K2CO3 (503 mg, 3.60 mmol) to a solution of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (500 mg, 2.40 mmol) in acetone (8 mL) at ambient temperature under N2. Add 1-bromomethyl-4-methoxybenzene (0.51 mL, 3.6 mmol) dropwise to the mixture, and stir overnight under N2. Quench the reaction with H2O, and extract twice with EtOAc. Dry the combined organic layers over MgSO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 0 to 15% EtOAc in hexanes) to yield the title compound (789 mg, quantitative). ES/MS m/z 351.0 (M+Na).

Workup

  1. customQuench
  2. customthe reaction with H2O
  3. extractionextract twice with EtOAc
  4. dry with materialDry the combined organic layers over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue by flash silica gel chromatography (gradient of 0 to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d066206ea5594fd1b834049fdf5b5dcf
Source dataset
uspto-grants-2013_08
Patent number
US08507490B2

Reaction notes

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