Reaktion #483945

Reaktionsgleichung

1-(4-bromophenyl)-4-methyl-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole

furan-3-boronic acid

NaHCO3

→

title compound

Ausbeute 13.3%

1-[4-(3-Furyl)phenyl]-4-methyl-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole

Ausbeute 13.3%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux temperature for 4 hours
3. 3
   FiltrationThe reaction mixture was filtered through celite
4. 4
   workup.ADDITIONthe filtrate was poured into water
5. 5
   Extraktionthe whole was extracted with ethyl acetate (10 mL×3)
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe residue was purified by thin-layer chromatography
10. 10
    Wascheneluting with hexane/ethyl acetate (3/1)
11. 11
    SonstigeThe resulting solid was recrystallized from CH2Cl2-hexane

Vorschrift

To a stirred solution of 1-(4-bromophenyl)-4-methyl-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole (0.08 g, 0.2 mmol) in DME (2.5 mL)was added furan-3-boronic acid (0.027 g, 0.24 mmol), bis(triphenylphosphine)palladium(II)chloride (0.016 g, 0.02 mmol) and saturated NaHCO3 solution (0.8 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 4 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by thin-layer chromatography eluting with hexane/ethyl acetate (3/1). The resulting solid was recrystallized from CH2Cl2-hexane to give the title compound (0.01 g, 13.3% yield).

Quelle