Potassium Carbonate → 4,6-Bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4'-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine

Participants

Reaction Steps

In a stream of argon, 0.54 g (2.42 mmol) of 9-phenanthreneboronic acid, 1.50 g (2.42 mmol) of 4,6-bis(biphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine and 56.0 mg (0.048 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 150 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.72 g (3.63 mmol) of 4-(2-pyridyl)phenylboronic acid and 7.26 mL (7.26 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 4 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 1.1 g of the target 4,6-bis(biphenyl-3-yl)-2-[5-(9-phenathryl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 58%).

Provenance & Evidence