Reaction #49470

Reaction equation

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

hydrochloric acid

1-(2-hydroxyethyl)piperazine

acetic acid

sodium triacetoxyborohydride

→

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

Yield 91.0%

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-ethyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (87.6 mg, 0.217 mmol) was dissolved in acetonitrile (7 mL), and the solution was treated with 1-(2-hydroxyethyl)piperazine (113 mg, 0.868 mmol), acetic acid (0.248 mL, 4.34 mmol) and sodium triacetoxyborohydride (184 mg, 0.868 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-ethyl-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (102 mg, yield 91%).

Source