Methyl chlorodifluoroacetate → Methyl 3-(trifluoromethyl)pyrazine-2-carboxylate
Reaction equation
Cl[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[F-:12].[K+].Cl[C:15]([F:21])([F:20])C(OC)=O>CN(C=O)C>[F:20][C:15]([F:21])([F:12])[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1Participants
5
Conditions
- Temperature
- 115 °C
Procedure
Methyl 3-chloropyrazine-2-carboxylate (2 g, 11.6 mmol), cuprous iodide (3.3 g, 17.3 mmol), potassium fluoride (1.34 g, 23 mmol) and methyl chlorodifluoroacetate (3.36 g, 18.2 mmol) were dissolved in DMF (20 ml) and stirred at 115° C. for 5 hours under argon atmosphere. The reaction solution was filtered with celite, followed by dilution of the filtrate with ethyl acetate, and washing four times with water. The filtrate was dried over magnesium sulfate, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=3:1)to obtain 700 mg of the desired compound as paste state.
Workup
- filtrationThe reaction solution was filtered with celite
- washwashing four times with water
- dry with materialThe filtrate was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue was purified
Sources & evidence
- ORD record
- ord-bd72b7ece836418eb9de47507a399f86
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08269045B2
Reaction notes
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