Tributylphosphine → 1-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)thiophen-2-yl)methoxy)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(1,2-dimethyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (200 mg) in THF (5 ml) were added (4-(trifluoromethyl)thiophen-2-yl)methanol (157 mg), 1,1′-(azodicarbonyl)dipiperidine (257 mg) and tributylphosphine (0.25 ml) at room temperature, and the mixture was stirred at 50° C. overnight. After cooling, the mixture was purified by NH silica gel column chromatography (EtOAc/MeOH), followed by preparative HPLC (C18, mobile phase: H2O/CH3CN (0.1% TFA included)). The desired fraction was neutralized with saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo to give the title compound (129 mg) as white crystals.

Provenance & Evidence