Ethyl bromoacetate → ethyl 5-ethyl-3-(trifluoromethyl)-1H-pyrazole-1-acetate
Reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:1]([C:3]1[N:7]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:6]=[C:5]([C:8]([F:10])([F:11])[F:9])[CH:4]=1)[CH3:2]Participants
5
Procedure
To a solution of 5-ethyl-3-(trifluoromethyl)-1H-pyrazole (1.39 g, 8.5 mmol) (i.e. the product of Example 16, Step A) in N,N-dimethylformamide (10 mL) was added potassium carbonate (2.3 g) and ethyl bromoacetate (1.4 mL, 12.6 mmol). The reaction mixture was stirred at room temperature overnight. The resulting solids were filtered off and the filtrate was diluted with ethyl acetate, washed with water and dried over MgSO4. The resulting solution was concentrated under reduced pressure to give 1.34 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.
Workup
- filtrationThe resulting solids were filtered off
- additionthe filtrate was diluted with ethyl acetate
- washwashed with water
- dry with materialdried over MgSO4
- concentrationThe resulting solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9080a836df1240f8a3ceff46ce2c9b6b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586611B2
Reaction notes
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