Reaktion #1076375

Reaktionsgleichung

2,3-Dihydro-7-iodo-5-nitrobenzofuran

3-pyridylboronic acid

sodium carbonate

→

title compound

Ausbeute 30.2%

2,3-Dihydro-5-nitro-7-(pyrid-3-yl)benzofuran

Ausbeute 30.2%

Lösungsmittel

1,2-dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 18 hours
3. 3
   Extraktionextracted into ethyl acetate
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated in vacuo
6. 6
   SonstigeThe residue was purified by flash column chromatography on silica gel
7. 7
   Wascheneluting with 30% ethyl acetate/60-80° petroleum ether

Vorschrift

2,3-Dihydro-7-iodo-5-nitrobenzofuran (0.76 g, 0.0026 mole) and 3-pyridylboronic acid (0.32 g, 0.0026 mole) in 50% aqueous 1,2-dimethoxyethane (50 ml) were treated under argon with sodium carbonate (1.17 g, 0.011 mole) and tetrakis triphenylphosphine palladium (0) (0.06 g, 0.000052 mole) and heated under reflux for 18 hours. The mixture was allowed to cool to ambient temperature, diluted with deionised water, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 30% ethyl acetate/60-80° petroleum ether to afford the title compound (0.19 g, 30%) as a yellow solid.

Quelle