Reaktion #2290242

Reaktionsgleichung

1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

(5-(trifluoromethyl)-2-thienyl)methanol

tributylphosphine

1,1′-(azodicarbonyl)dipiperidine

→

title compound

Ausbeute 17.6%

1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one

Ausbeute 17.6%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe extract was washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by NH silica gel column chromatography (hexane/EtOAc
7. 7
   SonstigeThe resulting solid was recrystallized from EtOH

Vorschrift

To a solution of 1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (120 mg), (5-(trifluoromethyl)-2-thienyl)methanol (162 mg) and tributylphosphine (270 mg) in THF (8 ml) was added 1,1′-(azodicarbonyl)dipiperidine (337 mg), and the reaction mixture was stirred at 60° C., for 2 h. The reaction mixture was cooled to room temperature. The mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH to give the title compound (33.9 mg) as a white solid.

Quelle