2-Bromo-6-phenylpyridine → HCID 58526502, compound

Participants

Reaction Conditions

Reaction Steps

In a stream of argon, tetrahydrofuran (3 mL) was cooled to −78° C. To the cooled tetrahydrofuran, a tetrahydrofuran solution (1.18 mL) of tert-butyllithium (1.58 mol/L) was added. Then a tetrahydrofuran solution (2 mL) of 2-bromo-6-phenylpyridine (211 mg) was dropwise added to the tert-butyllithium solution. The mixture was stirred for 15 minutes while the mixture was maintained at −78° C. To the reaction mixture, zinc chloride tetramethylethylenediamine complex (530 mg) was added to allow the temperature to rise naturally to room temperature. Then, to the reaction mixture, a tetrahydrofuran suspension (2 mL) having suspended therein 2,4-bis(5-bromobiphenyl-3-yl)-6-phenyl-1,3,5-triazine (185.8 mg) and tetrakis(triphenylphosphine)palladium (13.9 mg) was dropwise added. The resultant mixture was stirred at 50° C. for 19 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added, and the solid precipitate was recovered by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (2:1) mixed liquid as a developing solvent, to give 120 mg of the target 2,4-bis[5-(6-phenylpyridin-2-yl)biphenyl-3-yl]-6-phenyl-1,3,5-triazine as a white powder (yield: 52%).

Provenance & Evidence