Lithium Hydroxide → 5-(3-Trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid

HRID 1255792Notes

Reaction equation

HRID 1255792 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[N:12]2)=[CH:7][N:6]=1)=[O:4].[Li+].[OH-]>CO.C1COCC1.O>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:14]=[CH:15][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=2)[N:12]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 574965955-(3-Trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 574965965-(3-Trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acidYield 99.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid methyl ester (67 mg) in MeOH (4 ml) and THF (0.5 ml) was added a solution of LiOH (23 mg) in water (1 ml) and stirring was continued at 22° C. for 22 h. The mixture was evaporated and the residue partitioned between 1 N aqueous HCl and ethyl acetate, the organic layer was washed with water, dried and evaporated to give 5-(3-trifluoromethyl-pyrazol-1-yl)-pyridine-2-carboxylic acid (63 mg) as a white solid. MS (ESI): m/z=255.9 [M−H]−.

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between 1 N aqueous HCl and ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-bb77e6331505478dab99b6986ab6c764
Source dataset
uspto-grants-2013_06
Patent number
US08461160B2

Reaction notes

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