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
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
Product 1
Reagents, catalysts & solvents 1
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).