Cesium carbonate → Methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylate

HRID 1842234Notes

Reaction equation

HRID 1842234 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])(=O)=O.O[C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=1.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[F:15][C:14]([F:17])([F:16])[CH2:13][O:12][C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178498852HCID 178498852, compound

Product 1

HCID 57827340Methyl 5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxylateYield 18.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (2.96 g) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.57 g) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (700 mg) in DMF (20 mL), and the mixture was stirred at room temperature for 20 hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain the title compound (197 mg).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2256b49263ad4cd093127d56564c26fc
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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