Reaktion #584368

Reaktionsgleichung

2-methyl 5-[4-(methylsulfonyl)phenyl]-1-(4-bromophenyl)-1H-pyrrole

thiophene-3-boronic acid

NaHCO3

→

title compound

Ausbeute 75.0%

2-Methyl-5-[4-(methylsulfonyl)phenyl]-1-[4-(3-thienyl)phenyl]-1H-pyrrole

Ausbeute 75.0%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux temperature for 6 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 flash chromatography
10. 10
    Wascheneluting with hexane/ethyl acetate (4/1)
11. 11
    SonstigeThe resulting solid was recrystallized from ethyl acetate/hexane

Vorschrift

To a stirred solution of 2-methyl 5-[4-(methylsulfonyl)phenyl]-1-(4-bromophenyl)-1H-pyrrole (0.2 g, 0.51 mmol) in DME (6 mL) was added thiophene-3-boronic acid (0.079 g, 0.61 mmol), bis(triphenylphosphine)palladium(II)chloride (0.04 g, 0.06 mmol) and saturated NaHCO3 solution (2 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 6 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 flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from ethyl acetate/hexane to give the title compound (0.15 g, 75.0% yield).

Quelle