Reaktion #90071

Reaktionsgleichung

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

trimethyl boroxine

potassium carbonate

→

title compound

Ausbeute 59.6%

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

Ausbeute 59.6%

Lösungsmittel

N,N-dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

Under nitrogen atmosphere, to the N,N-dimethyl formamide (1.5 ml) solution 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, 50 mg, 0.099 mmol), trimethyl boroxine (12 mg, 0.1 eq.), tetrakis triphenylphosphine palladium (39 mg, 0.2 eq.), and potassium carbonate (41 mg, 3.0 eq.) were added, and the mixture was stirred at 100° C. for 24 hr. 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 the title compound (25 mg, 58%).

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