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

HRID 503163Notes

Reaction equation

HRID 503163 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(Br)(Br)Br.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 25134Boron tribromideHCID 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 tribromide 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-962eb9731fdf400db4dd311c2971c2c8
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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