Reaktion #626658

Reaktionsgleichung

N-phenyl-3-(quinolin-2-yl)aniline

sodium tert-butoxide

2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

→

3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(quinolin-2-yl)phenyl)aniline

Ausbeute 91.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture was evacuated
2. 2
   workup.ADDITIONback-filled with nitrogen
3. 3
   TemperaturThe reaction mixture was then heated
4. 4
   Temperaturat reflux for 20 h
5. 5
   workup.ADDITIONthen was diluted with 200 mL of water
6. 6
   SonstigeThe toluene layer was separated
7. 7
   Extraktionthe aqueous was extracted with 100 mL of toluene
8. 8
   Sonstigeremoved under vacuum

Vorschrift

N-phenyl-3-(quinolin-2-yl)aniline (3 g, 10.12 mmol), sodium tert-butoxide (1.555 g, 16.20 mmol), 2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (4.07 g, 10.63 mmol), Pd2dba3 (0.232 g, 0.253 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.415 g, 1.012 mmol) were charged into the reaction vessel with 250 mL of toluene. This mixture was evacuated and back-filled with nitrogen. The reaction mixture was then heated at reflux for 20 h. The reaction mixture was cooled to room temperature then was diluted with 200 mL of water. The toluene layer was separated and the aqueous was extracted with 100 mL of toluene. The organic extracts were combined and removed under vacuum. The crude residue was passed through a silica gel column using 5-25% ethyl acetate/DCM yielding 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(quinolin-2-yl)phenyl)aniline (5.5 g, 91% yield) as a yellow foamy solid.

Quelle