Acetic Acid → 4-Chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(methylsulfonyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone

Participants

Reaction Steps

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (40.7 mg, 0.0991 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 1-(methylsulfonyl)piperazine hydrochloride (80.0 mg, 0.399 mmol), triethylamine (0.110 mL, 0.789 mmol), acetic acid (0.115 mL, 2.01 mmol) and sodium triacetoxyborohydride (77.7 mg, 0.367 mmol). The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was 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 to obtain 4-chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(methylsulfonyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone (67.2 mg).

Provenance & Evidence