Reaction #49613

Reaction equation

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

(2-methoxyethyl)methylamine

acetic acid

sodium triacetoxyborohydride

→

4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-[N-(2-methoxyethyl)methylaminomethyl]indol-2-yl]isoindolinone

Yield 60.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherfollowed by purification by flash column chromatography (chloroform/methanol=4/1)

Procedure

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (856 mg, 1.71 mmol) was dissolved in acetonitrile (17.0 mL), and the solution was treated with (2-methoxyethyl)methylamine (2.76 mL, 25.7 mmol), acetic acid (1.47 mL, 25.7 mmol) and sodium triacetoxyborohydride (1.81 g, 8.56 mmol), followed by purification by flash column chromatography (chloroform/methanol=4/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-[N-(2-methoxyethyl)methylaminomethyl]indol-2-yl]isoindolinone (586 mg, 60%).

Source