Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:44][C:45]([CH3:47])=[CH2:46])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:46][C:45](=[O:44])[CH3:47])=[CH:10][CH:9]=2)=[O:5])[CH3:2]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester (3.28 g, 8.13 mmol), tributyltin methoxide (3.92 g, 3.51 ml, 12.2 mmol), isopropenyl acetate (1.22 g, 1.34 ml, 12.2 mmol), palladium (II) acetate (91 mg, 0.41 mmol) and tri-o-tolylphosphine (248 mg, 0.813 mmol) in toluene (10 ml) was heated at about 95° C. under nitrogen for about 3 hours. The reaction solution was cooled, concentrated in vacuo, and subjected to flash chromatography on silica (200 g, gradient from 10% ethyl acetate/hexane to 40% ethyl acetate/hexane), and then the partially pure product was recrystallized from toluene/heptane to give the title compound (1.91 g).
Aufarbeitung
- temperatureThe reaction solution was cooled
- concentrationconcentrated in vacuo
- customthe partially pure product was recrystallized from toluene/heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-04938e7e5b234ba98711ff0e387cc7b4
- Quelldatensatz
- uspto-grants-1999_01
- Patentnummer
- US05859044
Verknüpfte Notizen
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