Reaction #49507

Reaction equation

water

triethylamine

cyclopropanecarbonyl chloride

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

→

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

Yield 26.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer was washed with saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe solvent was evaporated under reduced pressure
5. 5
   Otherthe residue was purified by flash column chromatography (chloroform/methanol=85/15)

Procedure

4-Amino-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0940 g, 0.204 mmol) was dissolved in ethyl acetate (4.0 mL), and the solution was added with triethylamine (0.0570 mL, 0.408 mmol) and cyclopropanecarbonyl chloride (0.0280 mL, 0.306 mmol), followed by stirring at room temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=85/15) to obtain 4-cyclopropylcarbonylamino-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0280 g, yield 26%).

Source