Reaktion #49472

Reaktionsgleichung

water

trimethylboroxine

potassium carbonate

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

→

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

Ausbeute 86.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1)

Vorschrift

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (176 mg, 0.336 mmol) was dissolved in dimethoxyethane (8.8 mL), and the solution was treated with trimethylboroxine (0.140 mL, 1.01 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (32.9 mg, 0.0403 mmol), potassium carbonate (231 mg, 1.68 mmol) and water (0.121 mL), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1) to obtain 4-methyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (112 mg, yield 86%).

Quelle