(1-(4-Fluorophenyl)-1H-indazol-5-yl)methanol → 1-(4-fluorophenyl)-1H-indazole-5-carboxylic acid

HRID 218172Notes

Reaction equation

HRID 218172 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:21])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67005185(1-(4-Fluorophenyl)-1H-indazol-5-yl)methanolHCID 131709961Jones' reagent

Product 1

HCID 596259981-(4-fluorophenyl)-1H-indazole-5-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of (1-(4-fluorophenyl)-1H-indazol-5-yl)methanol (0.45 g, 1.9 mmol) in acetone (10 mL) was added Jones' reagent (3 mL) dropwise at 0° C. The reaction mixture was stirred at rt for 1 hr and concentrated under reduced pressure. Water was added to the residue and the solid that separates out was filtered, washed with water and dried to give 1-(4-fluorophenyl)-1H-indazole-5-carboxylic acid (0.43 g, 1.7 mmol, 89% yield) as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. filtrationthe solid that separates out was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-634776d34bd8431bb1426a48caffe808
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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