Sodium Chloride → Methyl 5-(2,2-difluoroethoxy)pyrazine-2-carboxylate

HRID 1842123Notes

Reaction equation

HRID 1842123 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH:9]([F:11])[F:10].[OH:12][C:13]1[N:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[N:17][CH:18]=1.[Cl-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[F:10][CH:9]([F:11])[CH2:8][O:12][C:13]1[N:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 1361862-Bromo-1,1-difluoroethaneHCID 178498852HCID 178498852, compound

Product 1

HCID 57827325Methyl 5-(2,2-difluoroethoxy)pyrazine-2-carboxylateYield 20.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (2.12 g) and 2-bromo-1,1-difluoroethane (939 mg) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (500 mg) in DMF (20 mL), and the mixture was stirred at 80° C. for four hours. The reaction solution was returned to room temperature. Saturated aqueous sodium chloride and ethyl acetate were added and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (145 mg).

Workup

  1. customwas returned to room temperature
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-354171b5c6404a8aa854e5bbc52efe19
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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