Reacción #49411

Ecuación de reacción

water

triethylamine

4-chloro-2-fluorobenzenesulfonyl chloride

4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

→

4-(2-fluoro-4-chlorobenzenesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Rendimiento 27.3%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was evaporated
2. 2
   workup.ADDITIONThe residue was added with water
3. 3
   Extracciónextracted with chloroform
4. 4
   LavadoThe organic layer was washed with saturated brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered through a column
7. 7
   workup.ADDITIONfilled with SCX (positive-ion exchange resin)
8. 8
   LavadoThe SCX was washed with 2 mol/L ammonia-methanol solution
9. 9
   Otrothe filtrate was evaporated

Procedimiento

4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0300 g, 0.0650 mmol) was dissolved in acetonitrile (0.650 mL), and the solution was added with triethylamine (0.0540 mL, 0.390 mmol) and 4-chloro-2-fluorobenzenesulfonyl chloride (0.0450 g, 0.195 mmol), followed by stirring at room temperature for 12 hours. The reaction mixture was added with water and the solvent was evaporated. The residue was added with water and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then filtered through a column filled with SCX (positive-ion exchange resin). The SCX was washed with 2 mol/L ammonia-methanol solution and the filtrate was evaporated to obtain 4-(2-fluoro-4-chlorobenzenesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0116 g, yield 27%).

Fuente