Reaktion #2289625

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

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

→

title compound

6,6,9-Trimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Lösungsmittel

N,N-dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeWith the same condition as the method for synthesizing the Compound
2. 2
   SonstigeUpon the completion of the reaction
3. 3
   workup.DISTILLATIONdistilled water
4. 4
   workup.ADDITIONwas poured into the reaction solution, which
5. 5
   Extraktionwas then extracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with aqueous solution of sodium chloride
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeThe drying agent was removed by filtration
9. 9
   Sonstigethe residues obtained
10. 10
    Einengenafter concentration under reduced pressure
11. 11
    Sonstigewere purified by silica gel column chromatography (ethyl acetate/methanol)
12. 12
    Sonstigeto obtain the Compound

Vorschrift

With the same condition as the method for synthesizing the Compound F5-47 (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 hours. Upon the completion of the reaction, distilled water was poured into the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with aqueous solution of sodium chloride 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 Compound F5-47 (8-(4-cyclobutyl-piperazin-1-yl)-6,6,9-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile) (25 mg, 58%)), the title compound was synthesized from the Compound F3-11.

Quelle