Reaktion #90069

Reaktionsgleichung

9-bromo-6,6-dimethyl-8-morpholin-4-yl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

3-bromopropyne

morpholine

X-Phos

cesium carbonate

→

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

Lösungsmittel

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   SonstigeThe drying agent was removed by filtration
4. 4
   Sonstigethe residues obtained
5. 5
   Einengenafter concentration under reduced pressure
6. 6
   Sonstigewere purified by silica gel column chromatography (dichloromethane/methanol)
7. 7
   Sonstigeto obtain the target compound (pale brown solid, 18 mg, 64%)

Vorschrift

To 9-bromo-6,6-dimethyl-8-morpholin-4-yl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound F3-4, 30 mg, 0.067 mmol), 3-bromopropyne (0.01 ml, 0.13 mmol), morpholine (0.029 ml, 0.33 mmol), X-Phos (4.8 mg, 15% mol), PdCl2 (CH3CN)2 (0.9 mg, 5% mol) and cesium carbonate (87 mg, 0.27 mmol), acetonitrile (2 ml) was added and the mixture was stirred at 80° C. for 2 hr. The reaction solution was added to water, and then extracted with dichloromethane. The organic layer was 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 (dichloromethane/methanol) to obtain the target compound (pale brown solid, 18 mg, 64%).

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