Reaktion #49499

Reaktionsgleichung

2,4,6-trivinylcyclotriboroxane-pyridine complex

potassium carbonate

water

4-trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

→

4-vinyl-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

Ausbeute 82.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1)

Vorschrift

In a similar manner to Step 1 of Example 152, 4-trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (46.0 mg, 0.0611 mmol) was dissolved in dimethoxyethane (2.8 mL), and the solution was treated with 2,4,6-trivinylcyclotriboroxane-pyridine complex (32 mg, 0.13 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (4.4 mg, 0.0054 mmol), potassium carbonate (46 mg, 0.34 mmol) and water (0.024 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1) to obtain 4-vinyl-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (31.6 mg, yield 82%).

Quelle