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

HRID 2421254Notes

Reaction equation

HRID 2421254 reaction equation
[F:1][C:2]1[C:3]([O:26]CC2C=CC=CC=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[C:13]([F:25])[CH:12]=1)[CH:6]=[CH:5]2>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[CH:6]=[CH:5][C:4]=2[C:3]=1[OH:26]

Participants

3

Reactant 1

HCID 596279345-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

Product 1

HCID 441931875-fluoro-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D7) (143 mg) in ethyl acetate (8 mL) was passed through the H-cube at 1 mL/min with 1 Bar H2 pressure. The solution was evaporated and purified by chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) to give the title compound (E5) as an off white solid (65 mg).

Workup

  1. customThe solution was evaporated
  2. custompurified by chromatography on silica gel (elution with 0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-46450c7833fe40f5a7c764256768e96d
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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