Dichloromethane → 2-Chloro-4-(4-chlorophenyl)-3,4'-bipyridine

Participants

Reaction Conditions

Reaction Steps

In a pressure tube, to a stirring solution of 3-bromo-2-chloro-4-(4-chlorophenyl)pyridine (1.3 g, 4.49 mmol) in THF (60 mL) at room temperature under argon was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.3 g, 11.21 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (350 mg, 0.43 mmol), and powdered K3PO4 (1.9 g, 8.96 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 12 h. After the reaction mixture was cooled to room temperature, water (40 mL) and EtOAc (50 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel column eluting with 20% ethyl acetate-hexanes) to isolate 850 mg of the title compound as a white solid. HPLC/MS: retention time=2.157 min, [M+H]+=301.

Provenance & Evidence