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

HRID 2421260

Reaktionsgleichung

Reaktionsgleichung von HRID 2421260
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([O:26]CC4C=CC=CC=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:16][C:6]1[CH:5]=[C:4]([N:17]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=3[CH:19]=[CH:18]2)[CH:3]=[C:2]([F:1])[C:7]=1[OH:8]

Komponenten

4

Edukt 1

HCID 596279281-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

Produkt 1

HCID 441932831-(3,5-difluoro-4-hydroxyphenyl)-1H-indol-4-olAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D21) (299 mg, 0.678 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) (150 mg). After 21 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage SP4) eluting with a gradient of 0 to 100% Et2O in hexane to give the title compound (E11), (61 mg).

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 21 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (Biotage SP4)
  5. washeluting with a gradient of 0 to 100% Et2O in hexane

Quellen und Nachweise

ORD-Eintrag
ord-9e4f8a5d2a2f4b4d9194426256e2f22a
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956083B2

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