HCID 59272956, Verbindung → HCID 135910367, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26]C)=[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)[N:8]=[CH:7]2>Br>[F: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)[N:8]=[CH:7][C:6]=2[C:5]([OH:26])=[CH:4][CH:3]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
7-Fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole (D27) (280 mg, 0.764 mmol) was dissolved in HBr (48% aq., 15 mL) and refluxed at 120° C. under argon. After 2 hours the mixture was partitioned between DCM (50 mL)/water (50 mL), the pH adjusted to 7 by addition of a 2M solution of NaOH and the layers separated. The aqueous phase was extracted with DCM (3×50 mL) and the combined organics were washed with brine (50 mL), separated and dried over MgSO4, filtered and concentrated in vacuo. The crude material (198 mg) was purified by flash chromatography (Biotage SP4) with a gradient of 0-100% Et2O in hexane. The isolated material (75 mg) was further purified by MDAP to afford 46 mg of the title compound (E13).
Aufarbeitung
- customAfter 2 hours the mixture was partitioned between DCM (50 mL)/water (50 mL)
- additionthe pH adjusted to 7 by addition of a 2M solution of NaOH
- customthe layers separated
- extractionThe aqueous phase was extracted with DCM (3×50 mL)
- washthe combined organics were washed with brine (50 mL)
- customseparated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material (198 mg) was purified by flash chromatography (Biotage SP4) with a gradient of 0-100% Et2O in hexane
- customThe isolated material (75 mg) was further purified by MDAP
Quellen und Nachweise
- ORD-Eintrag
- ord-93244fbac6b84eb1b7d15dceedc46e36
- Quelldatensatz
- uspto-grants-2011_06
- Patentnummer
- US07960563B2
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