Ethyl bromoacetate → ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate
Reaction equation
[Cl: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+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[Cl: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]=1Participants
6
Procedure
To a suspension of 5-chloro-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Example 10, Step C) (2.1 g, 12.3 mmol) and potassium carbonate (3.6 g, 26.0 mmol) in 20 mL of N,N-dimethylformamide was added ethyl bromoacetate (2.1 mL, 18.8 mmol), and the resulting mixture was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate, washed with water, and dried (MgSO4). The reaction mixture was concentrated under reduced pressure and further purified by medium-pressure liquid chromatography using 0-50% of ethyl acetate in hexanes as eluant to give 940 mg of the title compound as an oil.
Workup
- washwashed with water
- dry with materialdried (MgSO4)
- concentrationThe reaction mixture was concentrated under reduced pressure
- customfurther purified by medium-pressure liquid chromatography
Sources & evidence
- ORD record
- ord-46d1652ec4044d4ea42e3bd940041b51
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08449898B2
Reaction notes
Loading…