Methane → 1-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423094
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([O:25]CC4C=CC=CC=4)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1.C>C(O)C.C(OCC)(=O)C.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

6

Edukt 2

HCID 297MethaneHCID 592729821-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole

Produkt 1

HCID 1359069491-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-olAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

A mixture of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole (D2) (307 mg) in ethanol/ethyl acetate (˜50 mL, 1:1) was hydrogenated in the presence of 10% Pd on charcoal (150 mg) at atmospheric pressure and room temperature for 3 hrs. The mixture was filtered and concentrated and then chromatographed on silica gel (elution with 0-50% ethyl acetate in hexane) to give an off white solid. This was dissolved in ethyl acetate and stirred with charcoal (Norit SX+, 10 mg) for 30 minutes. The mixture was filtered and concentrated to give the title compound (E1) (144 mg).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customchromatographed on silica gel (elution with 0-50% ethyl acetate in hexane)
  4. customto give an off white solid
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d595ae9388a44a5999fdecedb542972d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960563B2

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