1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole → 1-(3,5-difluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421260Notes

Reaction equation

HRID 2421260 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]=[CH:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:16][C:6]1[CH:5]=[C:4]([N:17]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=3[CH:19]=[CH:18]2)[CH:3]=[C:2]([F:1])[C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 596279281-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

Product 1

HCID 441932831-(3,5-difluoro-4-hydroxyphenyl)-1H-indol-4-olYield 34.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D21) (299 mg, 0.678 mmoL) was dissolved in ethyl acetate (10 mL) and was hydrogenated at room temperature and atmospheric pressure in the presence of 10% palladium on charcoal (50% wet) (150 mg). After 21 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage SP4) eluting with a gradient of 0 to 100% Et2O in hexane to give the title compound (E11), (61 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 21 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (Biotage SP4)
  5. washeluting with a gradient of 0 to 100% Et2O in hexane

Sources & evidence

ORD record
ord-9e4f8a5d2a2f4b4d9194426256e2f22a
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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