反应详情

To Pd2(dba)3CHCl3 (60.1 mg, 5 mol %) and PPh3 (60.9 mg, 20 mol %) under a nitrogen atmosphere was added anhydrous DMF (0.5 mL). The resulting precipitate was stirred at room temperature for 30 minutes during which time the colour changed from red to yellow/orange. To this was added 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindole (626.4 mg, 1.16 mmol) dissolved in anhydrous DMF (1.0 mL). To the resulting red solution was then added Zn(CN)2. The resulting precipitate was then heated to 60° C. (bath temperature) and stirring was continued at that temperature for 4 hours. The mixture was allowed to cool to room temperature and diluted with EtOAc:toluene (1:1, 10 mL). The mixture was washed with H2O (6 mL). The aqueous phase was then extracted with EtOAc:toluene (1:1, 5 mL×5). The organic phases were combined and dried (anhydrous MgSO4). After filtration the solvent was removed in vacuo. The orange solid obtained was then purified by flash chromatography (silica gel, eluting 1% to 2% to 3%MeOH in CHCl3) to give the title compound as a light brown/orange solid (462.6 mg, 91%).

1. temperatureThe resulting precipitate was then heated to 60° C. (bath temperature)
2. stirringstirring
3. waitwas continued at that temperature for 4 hours
4. temperatureto cool to room temperature
5. washThe mixture was washed with H2O (6 mL)
6. extractionThe aqueous phase was then extracted with EtOAc:toluene (1:1, 5 mL×5)
7. dry with materialdried (anhydrous MgSO4)
8. filtrationAfter filtration the solvent
9. customwas removed in vacuo
10. customThe orange solid obtained
11. customwas then purified by flash chromatography (silica gel, eluting 1% to 2% to 3%MeOH in CHCl3)