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HRID 61786Erstellt: 24. Oktober 2026

Water → 8-Methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/de/reaction/61786

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
EduktPotassium vinyltrifluoroborateHCID 23679353—
Edukt9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 54578544—
Lösungsmittel1-PropanolHCID 1031—
Produkt8-Methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 6683418956,2%

Reaktionsbedingungen

Temperatur60 °C

Reaktionsschritte

9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E3-1-1, 50 mg, 0.13 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (1:1) (10.3 mg, 0.1 eq.), TEA (53 μl, 3 eq.) and potassium vinyltrifluoroborate (51 mg, 3 eq.) were dissolved in n-propanol and the mixture was stirred at 60° C. for 5 days. The reaction solution was added to water and then extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (brown powder, 25 mg, 19%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09440922B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-54492f4e782e40e88c592fe8d9e64e3b
Quellennotizuspto-grants-2016_09