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HRID 61784Erstellt: 24. Oktober 2026

Cesium carbonate → 9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/de/reaction/61784

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
EduktMethylbutynolHCID 148036—
Edukt2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
Edukt9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 54578544—
KatalysatorBis(acetonitrile)dichloropalladiumHCID 6093782—
LösungsmittelWaterHCID 962—
LösungsmittelAcetonitrileHCID 6342—
Produkt9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66834347281,6%

Reaktionsbedingungen

Temperatur85 °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), bis(acetonitrile)dichloropalladium (II) (1.64 mg, 0.05 eq.), XPhos (9.05 mg, 0.15 eq.), cesium carbonate (185 mg, 4.5 eq.) and 3-methyl-1-butyn-1-ol (18.6 μl, 1.5 eq.) were dissolved in acetonitrile and stirred at 85° C. for 2 hr. 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 HPLC to obtain the title compound (brown solid, 21.3 mg, 42%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09440922B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-0283fc9a817a4009991dc88d5add1d29
Quellennotizuspto-grants-2016_09