Cesium carbonate → HCID 57827374, compound

HRID 1842125Notes

Reaction equation

HRID 1842125 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:8][CH2:9][F:10].[OH:11][C:12]1[N:13]=[CH:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[N:16][CH:17]=1.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[F:10][CH2:9][CH2:8][O:11][C:12]1[N:13]=[CH:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 178498852HCID 178498852, compound

Product 1

HCID 57827374HCID 57827374, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (6.34 g) and 1-iodo-2-fluoroethane (2.26 g) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (1 g) in DMF (30 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 then 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 (200 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 column chromatography

Sources & evidence

ORD record
ord-476edc11d8cc4a549fda34b35128c969
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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