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

HRID 2423108Notes

Reaction equation

HRID 2423108 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([O:25]CC4C=CC=CC=4)[CH:21]=[CH:22][CH:23]=3)[C:18]([CH3:33])=[N:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>[Pd].C(OCC)(=O)C>[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[C:18]([CH3:33])=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 592729801-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-3-methyl-4-[(phenylmethyl)oxy]-1H-indazole

Product 1

HCID 1359103791-(3-Fluoro-4-hydroxyphenyl)-3-methyl-1H-indazol-4-olYield 56.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-3-methyl-4-[(phenylmethyl)oxy]-1H-indazole (D31) (0.45 g) and 10% palladium on charcoal (150 mg) in ethyl acetate (30 mL) was hydrogenated at atmospheric pressure for about 18 hrs. The mixture was filtered, concentrated and chromatographed (silica gel, 0-100% ethyl acetate in hexane) to give the title compound as a white solid (0.15 g) (E15).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customchromatographed (silica gel, 0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7bad8690b5cf4376a8f3d769efe82258
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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