1-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazol-4-ol → 1-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423095Notes

Reaction equation

HRID 2423095 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 1360852461-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazol-4-ol

Product 1

HCID 1359069491-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-olYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazol-4-ol (D39) (3.79 g, 11.3 mmol) in ethyl acetate (150 mL) was hydrogenated overnight at room temperature and pressure over 10% palladium on charcoal (700 mg). The mixture was filtered through a pad of celite, washed with ethyl acetate and the resulting filtrate was concentrated in vacuo. The product was purified by silica gel chromatography eluting with 5-80% ethyl acetate in hexane. The product was then triturated with hexane and the product collected by filtration and dried in a vacuum oven to yield the title compound (Ela) (2.35 g).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with ethyl acetate
  3. concentrationthe resulting filtrate was concentrated in vacuo
  4. customThe product was purified by silica gel chromatography
  5. washeluting with 5-80% ethyl acetate in hexane
  6. customThe product was then triturated with hexane
  7. filtrationthe product collected by filtration
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d0264642baa549768961c8c08ab0f303
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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