Reaktionsgleichung
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[C:14]([O-])(=[O:16])[CH3:15].[Tl+].C(OC=C)CCC.Cl>CN(C=O)C.C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:14](=[O:16])[CH3:15])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]Komponenten
9
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 4
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
A mixture of N-(2-Fluoro-4-iodophenyl)methanesulfonamide (13-3, 5 mmol) and palladium(II)acetate (0.15 nM, 0.034 g), 1,3-bisdiphenyl phosphinoprophan (0.3 mM, 0.124 g), thallium(I)acetate (5.5 mM, 1.450 g) and butylvinyl ether (10 mM, 1.3 mL) in DMF (10 mL) was heated at 95° C. for 19 h. The reaction mixture was cooled to room temperature, diluted with THF, treated with 10% HCl (10 mL) and stirred at room temperature. A mixture was diluted with EtOAc, washed with ammonium chloride solution three times and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes as eluant to 3′-Fluoro-4′-(methylsulfonylamino)acetophenone (13-6, LJO-363).
Aufarbeitung
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with ammonium chloride solution three times
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-1e154d2223aa4f1f859ba08d87aad887
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08642657B2
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