Hydrochloric Acid → HCID 22226942, compound

Participants

Reaction Conditions

Reaction Steps

To a pre-cooled (−78° C.) solution containing 8-chloro-2-(5-methoxy-1H-benzimidazol-1-yl)quinoline 138B (2.16 g, 7.0 mMol) in anhydrous DCM (28 mL) was added a 1.0 M solution of borontribromide in DCM (20.9 mL, 20.9 mMol). The cooling bath was removed and the reaction mixture stirred at ambient temperature under nitrogen for 22 hours. The reaction was quenched by the addition of aqueous 1 N NaOH to a pH of about 8.8. After stirring for about minutes, the suspended solids were removed by filtration. The solids were subsequently stirred briefly with 1 N NaOH (21 mL, 21 mMol) to hydrolyse remaining borate esters, and then neutralized by adding 1 N HCl (21 mL, 21 mMol). The solid precipitate was filtered off, stirred briefly with a small amount of warm EtOAc to remove traces of starting material, and re-filtered to give 1.91 g, mp>250° C., of the title product 138C.

Provenance & Evidence