Chloroform → 1-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone

HRID 1458563

Reaktionsgleichung

Reaktionsgleichung von HRID 1458563
[CH3:1][S:2]([CH2:5][C:6]1[C:15]([Cl:16])=[C:14]([Cl:17])[CH:13]=[C:12]2[C:7]=1[N:8]=[C:9]([O:20][CH3:21])[C:10]([O:18][CH3:19])=[N:11]2)(=[O:4])=[O:3].C(=O)(OCC=C)O[CH2:24][CH:25]=[CH2:26].C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][S:2]([CH:5]([C:6]1[C:15]([Cl:16])=[C:14]([Cl:17])[CH:13]=[C:12]2[C:7]=1[N:8]=[C:9]([O:20][CH3:21])[C:10]([O:18][CH3:19])=[N:11]2)[CH2:26][CH:25]=[CH2:24])(=[O:4])=[O:3]

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 84764Carbonic acid, di-2-propen-1-yl esterHCID 22097001HCID 22097001, Verbindung

Produkt 1

HCID 220970431-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)methyl methyl sulphone (50 mg, 0.142 mmol) (Preparation 29) and diallyl carbonate (41 μl, 40 mg, 0.285 mmol) in dry tetrahydrofuran (0.8 ml) was added via cannula to a mixture of tris(dibenzylideneacetone)dipalladium (0 ml).chloroform adduct (7.4 mg, 0.007 mmol) and 1,2-bis(diphenylphosphino)ethane (11.3 mg, 0.028 mmol) in dry tetrahydrofuran (0.6 ml) under nitrogen at room temperature. The mixture was stirred at room temperature for 5 minutes and then at reflux for 2 hours. The mixture was allowed to cool, was diluted with dichloromethane and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 3:1 hexane:ethyl acetate) to give 1-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone as a mixture of diastereoisomers (approximately 20:1 by

Aufarbeitung

  1. customat room temperature
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluting with 3:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c4bf802a88524de9a0c76808cdd6d492
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852016

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