1-(4-Fluorophenyl)-5-methoxy-1H-indazole → 1-(4-Fluorophenyl)-1H-indazol-5-ol

HRID 13186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 13186
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 593396221-(4-Fluorophenyl)-5-methoxy-1H-indazole

Produkt 1

HCID 593397691-(4-Fluorophenyl)-1H-indazol-5-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1-(4-fluorophenyl)-5-methoxy-1H-indazole (147f, 3.32 g, 13.7 mmol) in CH2Cl2 (40 mL, dried over 4 Å mol sieves). Borontribromide solution (1M in dichloromethane, 35 mL, 35 mmol) was added and the mixture was stirred at 50° C. for 80 min. The reaction mixture was cooled to r.t., diluted with dichloromethane and washed with ice-cold sat. aqueous NaHCO3. Crude title compound crystallised from the organic phase at 8° C. Re-crystallization from methanol-water afforded 1-(4-fluorophenyl)-1H-indazol-5-ol as light grey needles (1.88 g). From the mother liquor was obtained by crystallization (methanol-water) additional title compound (0.7 g). Total yield 2.58 g (82%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to r.t.
  2. washwashed with ice-cold sat. aqueous NaHCO3
  3. customCrude title compound crystallised from the organic phase at 8° C

Quellen und Nachweise

ORD-Eintrag
ord-452ab5d8ac224f9099d2b8bde42a19ad
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

Notizen zur Reaktion

Wird geladen…