Reaktion #49495

Reaktionsgleichung

2,4,6-trivinylcyclotriboroxane-pyridine complex

potassium carbonate

water

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

→

4-vinyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Ausbeute 67.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by preparative thin-layer chromatography (chloroform/methanol=8/1)

Vorschrift

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (60.0 mg, 0.114 mmol) was dissolved in dimethoxyethane (3.0 mL), and the solution was treated with 2,4,6-trivinylcyclotriboroxane-pyridine complex (55.0 mg, 0.228 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (7.4 mg, 0.0091 mmol), potassium carbonate (79 mg, 0.57 mmol) and water (0.041 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=8/1) to obtain 4-vinyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (36.0 mg, yield 67%).

Quelle