Reaktion #483938

Reaktionsgleichung

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

thiazole

n-BuLi

→

title compound

Ausbeute 13.2%

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

Ausbeute 13.2%

Lösungsmittel

THF

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 30 minutes at −78° C
2. 2
   TemperaturThe reaction mixture was warmed to 0° C.
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturat reflux temperature for 19 hours
5. 5
   Temperaturcooled down to room temperature
6. 6
   FiltrationThe reaction mixture was filtered through celite
7. 7
   workup.ADDITIONthe filtrate was poured into water
8. 8
   Extraktionthe whole was extracted with ethyl acetate (20 mL×3)
9. 9
   WaschenThe organic layer was washed with brine
10. 10
    Trocknendried over Na2SO4
11. 11
    Einengenconcentrated in vacuo
12. 12
    SonstigeThe residue was purified by flash chromatography
13. 13
    Wascheneluting with hexane/ethyl acetate (2/1)
14. 14
    SonstigeThe resulting solid was recrystallized from CH2Cl2/hexane

Vorschrift

To a stirred solution of thiazole (0.072 g, 0.85 mmol) in anhydrous ether (2 mL) was added n-BuLi (0.58 mL, 1.61 M solution in hexane, 0.94 mmol) at −78° C. under nitrogen, the mixture was stirred for 30 minutes at −78° C., and then zinc chloride (2.55 mL, 1.0 M solution in ether, 2.55 mmol) was added at −78° C., the mixture was stirred for 30 minutes at −78° C. The reaction mixture was warmed to 0° C., and added the solution of 2-methyl 5-[4-(methylsulfonyl)phenyl]-1-(4-bromophenyl)-1H-pyrrole (0.3 g, 0.77 mmol) in THF (5 mL), tetrakis(triphenylphosphine)palladium (0) (0.088 g, 0.08 mmol). The reaction mixture was heated at reflux temperature for 19 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 (20 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 (2/1). The resulting solid was recrystallized from CH2Cl2/hexane to give the title compound (0.040 g, 13.2% yield).

Quelle