Dimethyl Sulfoxide → 4-((1-(4-fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzoic acid

HRID 563432Notes

Reaction equation

HRID 563432 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]([CH:17]([OH:26])[C:18]4[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][CH:19]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CS(C)=[O:29].[OH-:31].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([OH:26])[C:18]4[CH:25]=[CH:24][C:21]([C:22]([OH:29])=[O:31])=[CH:20][CH:19]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 670055114-((1-(4-fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzonitrile

Product 1

HCID 670059404-((1-(4-fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-((1-(4-Fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzonitrile (180 mg, 0.52 mmol) was dissolved in MeOH (5 mL) and DMSO (5 mL) and treated with 1 M NaOH (5 mL) at 100° C. After 36 h, the MeOH was removed in vacuo, the residue acidified with sat KH2PO4 to pH 4-5 and extracted with EtOAc×3. The organic layer was dried with MgSO4, filtered, concentrated in vacuo to give 180 mg (95% yield) of 4-((1-(4-fluorophenyl)-1H-indazol-5-yl)(hydroxy)methyl)benzoic acid. MS found: (M+H)+=362.

Workup

  1. customthe MeOH was removed in vacuo
  2. extractionextracted with EtOAc×3
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21797d5b0dec42c19bb765450eeda260
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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