Reaktion #43633

Reaktionsgleichung

water

7-bromo-3,4-dihydro-1(2H)-isoquinolinone

2,4,6-trivinylcyclotriboroxane

water

K2CO3

→

product

Ausbeute 88.0%

7-ethenyl-3,4-dihydro-1(2H)-isoquinolinone

Ausbeute 88.0%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux for 1.5 h
3. 3
   ExtraktionThe mixture was extracted with 10% methanol/dichloromethane (3×100 ml)
4. 4
   Trocknenthe organic layers were dried with magnesium sulphate
5. 5
   Sonstigeevaporated
6. 6
   WaschenChromatography on silica, eluting with 0-100% ethyl acetate/hexane

Vorschrift

A solution of 7-bromo-3,4-dihydro-1(2H)-isoquinolinone (0.679 g, 3.004 mmol) and tetrakis(triphenylphosphine)palladium(0) (174 mg, 0.150 mmol) in 1,2-dimethoxyethane (30 ml) was stirred at room temperature for 0.5 h before addition of 2,4,6-trivinylcyclotriboroxane.pyridine complex (for a synthesis see Kerins, Fergal; O'Shea, Donal F. J. Org. Chem. (2002), 67(14), 4968) (295 mg, 1.218 mmol), K2CO3 (415 mg, 3.004 mmol) and water (10 ml). The reaction was heated at reflux for 1.5 h before cooling to room temperature and addition of water (50 ml). The mixture was extracted with 10% methanol/dichloromethane (3×100 ml), the organic layers were dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (456 mg, 88%).

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