1-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-6-(methyloxy)-1H-indazol-4-ol → 1-(3-Fluoro-4-hydroxyphenyl)-6-(methyloxy)-1H-indazol-4-ol

HRID 2423096Notes

Reaction equation

HRID 2423096 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[C:22]([O:25][CH3:26])[CH:21]=[C:20]([OH:27])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[C:22]([O:25][CH3:26])[CH:21]=[C:20]([OH:27])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 1

HCID 1360852391-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-6-(methyloxy)-1H-indazol-4-ol

Product 1

HCID 1359103841-(3-Fluoro-4-hydroxyphenyl)-6-(methyloxy)-1H-indazol-4-olYield 74.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-6-(methyloxy)-1H-indazol-4-ol (D4) (116 mg, 0.32 mmol) in ethanol (5 mL) and ethyl acetate (5 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated and the product purified by silica gel chromatography eluting with 5-80% ethyl acetate in hexane to yield the title compound (E2) (65 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe product purified by silica gel chromatography
  3. washeluting with 5-80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-07d0653be5ff4f39a21ee63b165f2cc2
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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