Hydrochloric Acid → 1-{5-chloro-1-[3-(trifluoromethyl)phenyl]-1H-indol-2-yl}heptan-1-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.I[C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu]Br.CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 180 °C
Versuchsvorschrift
A mixture of 1-(5-chloro-1H-indol-2-yl)heptan-1-one (9.14 g) synthesized above, 3-iodobenzotrifluoride (1.97 mL), copper (I) bromide (327 mg), potassium carbonate (2.36 g) and N-methyl-2-pyrrolidone (30 mL) was deaerated, and the mixture was stirred under argon atmosphere at 180° C. for 1 day. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title object compound (0.78 g, 17%) as a brown oil.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-63b93bbe090d4ca5b63c8163f05c29a6
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08436043B2
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