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