1-{3,5-Difluoro-4-[(phenyl methyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole → 1-(3,5-Difluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423112Notes

Reaction equation

HRID 2423112 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([O:26]CC4C=CC=CC=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[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:17]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=3[CH:19]=[N:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[OH:8]

Participants

5

Reactant 1

HCID 592729551-{3,5-Difluoro-4-[(phenyl methyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole

Product 1

HCID 1359103831-(3,5-Difluoro-4-hydroxyphenyl)-1H-indazol-4-olYield 82.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole (D35) (257 mg, 0.58 mmol) in ethanol (10 mL) and ethyl acetate (10 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated and then the crude product purified by silica gel chromatography eluting with 5-100% ethyl acetate in hexane to yield the title compound (E19) (126 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe crude product purified by silica gel chromatography
  3. washeluting with 5-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e63e08888c0d431ab41f7219684f3009
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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