p-Toluenesulfonic acid → HCID 71272259, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-fluoro-3H-benzo[d]imidazole-5-carbonitrile (1.78 g, 11.1 mmol), DHP (1.84 g, 22.2 mmol), and TsOH (212 mg, 1.1 mmol) in THF (20 mL) under nitrogen was heated at 85° C. overnight. The reaction mixture was quenched with water (40 mL) and extracted with EtOAc (50 ml×2). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting petroleum ether:EtOAc (5:1) to afford 5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-6-carbonitrile as white solid (2.0 g, 73.8%).

Provenance & Evidence