Reaktionsgleichung
[C:1]1([S:7]([CH2:10][CH2:11]O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C.Br[C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][CH:34]=[CH:33]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:1]1([S:7]([CH:10]=[CH:11][C:30]2[CH:31]=[C:32]3[C:36](=[CH:37][CH:38]=2)[NH:35][CH:34]=[CH:33]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
8
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To 0.186 g (1.0 mmol) of 2-(phenylsulfonyl)ethanol, 3 ml of acetonitrile was added, followed by 0.19 g(1.1 mmol) of methanesulfonic anhydride and 0.56 ml (4.0 mmol) of triethylamine, and the mixture was stirred for 5 hours at an internal temperature of 50° C. Subsequently, 0.29 g (1.5 mmol) of 5-bromoindole, 0.011 g (0.05 mmol) of palladium acetate, and 0.067 g (0.22 mmol) of tri(o-tolyl)phosphine were added, and the mixture was then refluxed for 17 hours. After cooled to room temperature, the reaction mixture was concentrated and purified by column chromatography (hexane/ethyl acetate=70/30) to obtain 0.066 g of 5-[2-(phenylsulfonyl)ethenyl]indole. Yield: 23%.
Aufarbeitung
- temperaturethe mixture was then refluxed for 17 hours
- temperatureAfter cooled to room temperature
- concentrationthe reaction mixture was concentrated
- custompurified by column chromatography (hexane/ethyl acetate=70/30)
Quellen und Nachweise
- ORD-Eintrag
- ord-90fb7022e82a4cb485d643bf37510e97
- Quelldatensatz
- uspto-grants-2001_03
- Patentnummer
- US06201131B1
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