Reaction #49516

Reaction equation

4,5-dichloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

hydrochloric acid

1-(2-hydroxyethyl)piperazine

acetic acid

sodium triacetoxyborohydride

→

4,5-dichloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

Yield 94.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic layer was washed with sodium carbonate and saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe solvent was evaporated under reduced pressure

Procedure

In a similar manner to Step 2 of Example 6, 4,5-dichloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (115 mg, 0.258 mmol) was dissolved in acetonitrile (8.1 mL), and the solution was treated with 1-(2-hydroxyethyl)piperazine (134 mg, 1.03 mmol), acetic acid (0.295 mL, 5.16 mmol) and sodium triacetoxyborohydride (191 mg, 0.903 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with sodium carbonate and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4,5-dichloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (136 mg, yield 94%).

Source