Lithium Hydroxide → 5-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid

HRID 1865876Notes

Reaction equation

HRID 1865876 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]([F:18])=[CH:14][CH:13]=2)[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1.O>[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:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 866169575-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 866169585-Bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acidYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.81 g 5-bromo-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester in 10 ml tetrahydrofuran was added at room temperature 2.6 ml of a 1M solution of lithium hydroxide in water and the mixture was stirred for 15 minutes. The resulting solution was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic layer washed with water and brine. The organic phase was dried over magnesium sulfate and evaporated to yield 0.78 g of the title compound as white crystals. MS (ISP) (M+H+)=297.2 and 299.0.

Workup

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

Sources & evidence

ORD record
ord-fed9016c8f11439eb9a9384bac4b16da
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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