Potassium Carbonate → ethyl 5-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetate

HRID 238680Notes

Reaction equation

HRID 238680 reaction equation
[Br:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[N:6]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 178506065HCID 178506065, compound2×

Product 1

HCID 68745175ethyl 5-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 5-bromo-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Example 11, Step B) (2.73 g, 12.7 mmol) and potassium carbonate (2.0 g, 14.5 mmol) in N,N-dimethylformamide (20 mL) was treated with ethyl iodoacetate (3.0 ml, 25.3 mmol), and the resulting mixture was stirred at 95° C. for 3 h. The resulting mixture was diluted with ethyl acetate, washed with water, and dried (MgSO4). The reaction mixture was concentrated in vacuo and further purified by medium-pressure liquid chromatography using 0-50% of ethyl acetate in hexanes as eluant to give 2.84 g of the title compound as a brown oil.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customfurther purified by medium-pressure liquid chromatography

Sources & evidence

ORD record
ord-5c45e7e55ad94074b5e0d074123548b0
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

Loading…