Tetrahydrofuran → 1-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine
Reaktionsgleichung
[F:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+:26].[Na].O1CCCC1>CO.C(#N)C>[F:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:26])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
A mixture of 1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (0.32 g, 1.1 mmol) and ammonium acetate (0.871 g, 11.3 mmol) in methanol (3.0 mL) and acetonitrile (3.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohyride in tetrahydrofuran (2.8 mL, 2.8 mmol). The reaction was heated at 65° C. overnight, then cooled to room temperature and quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined extracts were dried over MgSO4 and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C17H15F2N2 (M+H)+: m/z=285.1; Found: 285.1.
Aufarbeitung
- temperatureAfter cooling to room temperature, to the resulting mixture
- temperatureThe reaction was heated at 65° C. overnight
- temperaturecooled to room temperature
- customquenched with sat. NaHCO3 solution
- extractionextracted with dichloromethane
- dry with materialThe combined extracts were dried over MgSO4
- customevaporated to dryness
Quellen und Nachweise
- ORD-Eintrag
- ord-69f45e4ef9c0478c90ff58f7181934fa
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08680108B2
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