HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
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
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | Methylbutynol | HCID 148036 | — |
| Edukt | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Edukt | 9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile | HCID 54578544 | — |
| Katalysator | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | 9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile | HCID 66834347 | 281,6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09440922B2 |
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| Quelldatensatz | uspto-grants-2016_09 |
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| ORD ID | ord-0283fc9a817a4009991dc88d5add1d29 |
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| Quellennotiz | uspto-grants-2016_09 |
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