7-bromo-5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole → 7-bromo-5-fluoro-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421253Notes

Reaction equation

HRID 2421253 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:34])[C:5]([O:26]CC2C=CC=CC=2)=[C:6]2[C:10]=1[N:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[C:13]([F:25])[CH:12]=1)[CH:8]=[CH:7]2>C(OCC)(=O)C.[Pd]>[Br:1][C:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[CH:8]=[CH:7][C:6]=2[C:5]([OH:26])=[C:4]([F:34])[CH:3]=1

Participants

4

Reactant 1

HCID 596279357-bromo-5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

Product 1

HCID 441824137-bromo-5-fluoro-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 7-bromo-5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D6) (442 mg, 0.849 mmol) in ethyl acetate (20 mL) was hydrogenated in the H-cube over 10% Pd—C at a flow rate of 1 mL/min. The product mixture was evaporated and chromatographed (silica gel, ethyl acetate in hexane) to give material that was further purified by MDAP to give the title compound (E4) as an off white solid. (84 mg)

Workup

  1. customThe product mixture was evaporated
  2. customchromatographed (silica gel, ethyl acetate in hexane)
  3. customto give material that
  4. customwas further purified by MDAP

Sources & evidence

ORD record
ord-e9309f5a715d483e90afc5959ca55c4d
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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