1-Piperidinecarboxaldehyde → (2,2'-Bipyridine)-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of commercially available 6-bromo-2,2′-bipyridine (600 mg; 2.55 mmol) in anh. THF (10 ml) was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.60 ml; 2.56 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 30 min. Piperidine-1-carbaldehyde (577 mg; 5.10 mmol) was added dropwise to the cooled (−78° C.) reaction mixture, and stirring was continued at −78° C. for 30 min. Aq. sat. NH4Cl (25 ml) and AcOEt (50 ml) were added, and the separated organic layer was further washed with brine (20 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (toluene/AcOEt=8/2) afforded [2,2′-bipyridine]-6-carbaldehyde as a dark-purple solid. LC-MS (conditions C): tR=0.75 min.; [M+H]+: 185.24 g/mol.

Provenance & Evidence