Reaktion #1977599

Reaktionsgleichung

(+/−)-4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-benzamide

4-bromofluorobenzene

sodium tert-butoxide

tri-tert-butylphosphine

sodium carbonate

→

pure product

Ausbeute 38.4%

(+/−)-4-Chloro-N-[7-(4-fluoro-phenyl)-4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl]-2-methoxy-benzamide

Ausbeute 38.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 4 h30
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Extraktionthe resulting solution extracted with dichloromethane
4. 4
   WaschenThe combined extracts were washed with saturated aqueous sodium chloride
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 90/10/1

Vorschrift

A mixture containing 0.035 g (0.08 mmol) of (+/−)-4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-benzamide, 0.016 g (0.09 mmol) of 4-bromofluorobenzene, 0.009 g (0.10 mmol) of sodium tert-butoxide, 0.006 g (0.03 mmol) of tri-tert-butylphosphine and 0.007 g (0.01 mmol) of tris(dibenzylideneacetone)dipalladium(0) in 1.60 mL of anhydrous toluene under argon atmosphere was stirred under reflux for 4 h30. The reaction mixture was cooled, aqueous solution of sodium carbonate was added and the resulting solution extracted with dichloromethane. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 90/10/1 to afford 0.016 g (38%) of the pure product as a powder.

Quelle