Réaction #45974

Équation de réaction

Et2O

N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine

DMF

1-[4-(benzyloxy)phenyl]-2-bromoethanone

→

desired product

diethyl-[3-(4-{2-isobutyl-4-[4-(4-phenoxy-benzyloxy)-phenyl]-imidazol-1-yl}-phenoxy)-propyl]-amine

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   LavageThe combined organic layers were washed with brine
2. 2
   Séchagedried over sodium sulfate
3. 3
   AutreEvaporation of solvent in vacuuo

Mode opératoire

To a stirred solution of N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine (1.0 eq., 2.5 mmol) in anhydrous DMF (20 mL) DIEA (3 eq) was added, followed by slow addition of the 1-[4-(benzyloxy)phenyl]-2-bromoethanone (2.5 mmol). The reaction mixture was stirred under nitrogen at rt until completion, as indicated by HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in Et2O. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was purified by chromatography (Silica gel). Pure product was obtained by elution with 2-7% MeOH/DCM (yield˜30%).

Source