Water → 3-(3-Fluoro-phenyl)-6-hydroxy-1H-indazole-5-carboxylic Acid

HRID 1983503Notes

Reaction equation

HRID 1983503 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([O:20]C)=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[B].O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:20])=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5462311BoronHCID 222609563-(3-Fluoro-phenyl)-6-methoxy-1H-indazole-5-carboxylic Acid

Product 1

HCID 1355506963-(3-Fluoro-phenyl)-6-hydroxy-1H-indazole-5-carboxylic AcidYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A total of 96.2 mg of 3-(3-fluoro-phenyl)-6-methoxy-1H-indazole-5-carboxylic acid obtained in Production Example II-1-e was dissolved in 3.36 ml of dichloromethane, 4.0 ml of a 1.0 M solution of boron tribormide in dichloromethane was added under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, followed by extracting with ethyl acetate. The resulting organic layer was washed brine, dried over magnesium sulfate and the solvent was evaporated, to give 84.1 mg of the crude product of the title compound.

Workup

  1. temperaturecooling
  2. extractionby extracting with ethyl acetate
  3. washThe resulting organic layer was washed brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bb274adddf8a48b29fe4bb674cc3f668
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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