Acetic Acid → 4-Hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone

Participants

Reaction Steps

In a similar manner to Step 2 of Example 6, a crude product of 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.713 g) was dissolved in acetonitrile (20 mL), and the solution was treated with dimethylamine hydrochloride (2.75 g, 33.8 mmol), triethylamine (4.70 mL, 33.8 mmol), acetic acid (1.90 mL, 33.8 mmol) and sodium triacetoxyborohydride (1.10 g, 5.07 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=4/1) to obtain 4-hydroxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(dimethylaminomethyl)indol-2-yl]isoindolinone (0.138 g, yield 19%).

Provenance & Evidence