Reaktion #2362350

Reaktionsgleichung

9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

ethynyltriisopropylsilane

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

cesium carbonate

→

8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-[(triisopropylsilanyl)-ethynyl]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Ausbeute 74.5%

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturheated
3. 3
   Temperaturunder reflux condition until the reaction
4. 4
   SonstigeUpon the completion of the reaction
5. 5
   workup.DISTILLATIONdistilled water
6. 6
   workup.ADDITIONwas added to the reaction solution, which
7. 7
   Extraktionwas then extracted with ethyl acetate
8. 8
   WaschenThe organic layer was washed with brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    SonstigeThe drying agent was removed by filtration
11. 11
    Sonstigethe residues obtained
12. 12
    Einengenafter concentration under reduced pressure
13. 13
    Sonstigewere purified by silica gel column chromatography (ethyl acetate/methanol)

Vorschrift

Under nitrogen atmosphere, to the MeCN (8 ml) suspension of 9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound F4-10, 200 mg, 0.397 mmol), ethynyltriisopropylsilane (268 mg, 3.0 eq.), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (39 mg, 0.2 eq.), Pd(CH3CN)2Cl2 (11 mg, 0.1 eq.) and cesium carbonate (518 mg, 4.0 eq.) were added and the mixture was stirred and heated under reflux condition until the reaction is completed. Upon the completion of the reaction, distilled water was added to the reaction solution, which was 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/methanol) to obtain 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-[(triisopropylsilanyl)-ethynyl]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (179 mg, 74%).

Quelle