Acetic Acid → 4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(4-bromopiperidinomethyl)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 (42.7 mg, 0.104 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 4-bromopiperidine hydrobromide (105 mg, 0.428 mmol), acetic acid (0.120 mL, 2.10 mmol) and sodium triacetoxyborohydride (51.1 mg, 0.241 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-bromopiperidinomethyl)indol-2-yl]isoindolinone (77.3 mg).

Provenance & Evidence