Water → HCID 86616969, compound

HRID 1865884Notes

Reaction equation

HRID 1865884 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([Br:11])=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[N:6]=1)=[O:4].[OH-].[Li+].O>O1CCCC1>[Br:11][C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]([F:21])([F:20])[F:22])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86616968HCID 86616968, compound

Product 1

HCID 86616969HCID 86616969, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.38 g (0.016 mol) 5-bromo-6-(4-trifluoromethoxy-phenyl)-pyrazine-2-carboxylic acid methyl ester in 120 ml tetrahydrofuran was added at room temperature 17 ml of a 1M lithium hydroxide solution in water (0.017 mol) and the mixture was stirred at room temperature for 45 minutes. The resulting clear reaction mixture was partitioned between 10% aqueous citric acid solution and ethyl acetate. The phases were separated and the organic layer washed with water and brine, dried over magnesium sulfate and evaporated to yield 6.05 g (99% yield) of the title compound as white crystalline solid. MS (ISP) (M+H+)=363.0 and 364.9

Workup

  1. customThe resulting clear reaction mixture was partitioned between 10% aqueous citric acid solution and ethyl acetate
  2. customThe phases were separated
  3. washthe organic layer washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f96209add0894b8eb0854d86279cc3d0
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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