6-Ethenyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol → 6-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423101Notes

Reaction equation

HRID 2423101 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([OH:20])[C:6]2[CH:7]=[N:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:19])[CH:13]=3)[C:10]=2[CH:11]=1)=[CH2:2]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:20])[C:6]2[CH:7]=[N:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:19])[CH:13]=3)[C:10]=2[CH:11]=1)[CH3:2]

Participants

5

Reactant 1

HCID 1359103606-Ethenyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

Product 1

HCID 1359103616-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-olYield 18.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-ethenyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol (E6) (190 mg, 0.70 mmol) in ethanol (6 mL) and ethyl acetate (6 mL) was hydrogenated over a weekend at room temperature and a pressure of 50 psi over a 10% palladium on charcoal catalyst (20 mg). After filtration to remove the catalyst, the filtrate was concentrated and the crude product purified using MDAP to yield the title compound (E7) (36 mg).

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. customthe crude product purified

Sources & evidence

ORD record
ord-823a515e048f470994e4d41f24ee8083
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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