1-{2,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole → 1-(2,5-difluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421261Notes

Reaction equation

HRID 2421261 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]CC2C=CC=CC=2)[C:5]([F:16])=[CH:4][C:3]=1[N:17]1[C:25]2[C:20](=[C:21]([O:26]CC3C=CC=CC=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:16])=[CH:4][C:3]=1[N:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=2[CH:19]=[CH:18]1

Participants

4

Reactant 1

HCID 596279201-{2,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

Product 1

HCID 441932841-(2,5-difluoro-4-hydroxyphenyl)-1H-indol-4-olYield 74.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-{2,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D22) (258 mg, 0.584 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) (120 mg). After 22 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by MDAP to give the title compound (E12), (114 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 22 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by MDAP

Sources & evidence

ORD record
ord-3c1517c048f34e788187682935c9e9d7
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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