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
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]=1Participants
4
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)