Sodium borohydride → 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)ethanol
Reaktionsgleichung
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[N:21][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH2:28][C:29](OCC)=[O:30])[CH:27]=4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[BH4-].[Na+].C(Cl)Cl.O>CCO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:12][CH2:13][N:14]([C:17]3[N:22]=[N:21][C:20]([C:23]4[CH:24]=[N:25][N:26]([CH2:28][CH2:29][OH:30])[CH:27]=4)=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)=[CH:4][CH:3]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a solution of ethyl 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)acetate (90 mg, 0.2 mmol) in EtOH (3 mL) was added NaBH4 (76 mg, 2 mmol). The resulting mixture was heated at 65° C. for 2 h and then poured into CH2Cl2/H2O (50 mL/50 mL). The aqueous layer was extracted with CH2Cl2 (50 ml). The combined organic layer was dried (Na2SO4) and filtered. The solvent was removed and the resulting residue was purified by silica gel column using EtOAc to 2% MeOH/EtOAc as the eluent to yield 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)ethanol.
Aufarbeitung
- extractionThe aqueous layer was extracted with CH2Cl2 (50 ml)
- dry with materialThe combined organic layer was dried (Na2SO4)
- filtrationfiltered
- customThe solvent was removed
- customthe resulting residue was purified by silica gel column
Quellen und Nachweise
- ORD-Eintrag
- ord-aff51d00d59d46e0a954fbddd272ea66
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09102669B2
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