Reaktion #2290160

Reaktionsgleichung

1,1′-(azodicarbonyl)dipiperidine

1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one

(5-(trifluoromethyl)thiophen-2-yl)methanol

tributylphosphine

→

title compound

Ausbeute 35.2%

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

Ausbeute 35.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   Sonstigethe residue was purified by silica gel column chromatography (hexane/EtOAc
3. 3
   SonstigeThe resulting solid was recrystallized from EtOAc-EtOH

Vorschrift

To a mixture of 1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg), (5-(trifluoromethyl)thiophen-2-yl)methanol (130 mg) and tributylphosphine (0.26 ml) in THF (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (269 mg), and the mixture was stirred at 60° C. overnight. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH), followed by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOAc-EtOH to give the title compound (55.7 mg) as an off-white solid.

Quelle