Reaktion #60999

Reaktionsgleichung

tributyl(1-ethoxyvinyl)tin

1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

HCl

→

title compound

Ausbeute 10.0%

1-{4-[4-(5-Acetyl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

Ausbeute 10.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated to 100IC for 6 hours
2. 2
   TemperaturThe mixture was cooled in an ice bath
3. 3
   FiltrationThe mixture was filtered
4. 4
   SonstigeThe organic layer was separated
5. 5
   workup.ADDITION10% aqueous KF solution was added
6. 6
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
7. 7
   Filtrationfiltered
8. 8
   TrocknenThe organic layer was dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Sonstigethe solvent was removed in vacuo
11. 11
    SonstigeThe crude gum was chromatographed on silica gel, eluent

Vorschrift

To a suspension of 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (160 mg, 0.33 mmol) in toluene (2 ml) were added PdCl2(PPh3)2 (5 mg, 0.0065 mmol) and tributyl(1-ethoxyvinyl)tin (125 ul, 0.36 mmol). The mixture was heated to 100IC for 6 hours. The mixture was cooled in an ice bath and 2N HCl (0.55 ml) was added. The mixture was stirred at room temperature overnight. The mixture was filtered. The organic layer was separated and 10% aqueous KF solution was added. The mixture was stirred at room temperature for 3 hours and filtered. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude gum was chromatographed on silica gel, eluent: heptane/ethylacetate 0%-50% (10 minutes) to provide the title compound (15 mg, 10%) as a white solid MS (m/e): 454.2 (M+H, 100%).

Quelle