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

Participants

Reaction Steps

In a stream of argon, 5.00 g (10.7 mmol) of 9-phenanthreneboronic acid, 2.38 g (10.7 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 124 mg (0.107 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 400 mL of toluene and 50 mL of ethanol, and the resultant suspension was heated to 50° C. To the suspension, 32.1 mL (32.1 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. The resultant reaction mixture was cooled to room temperature, and then, 3.19 g (10.7 mmol) of 3-(2-pyridyl)phenylboronic acid and 32.1 mL (32.1 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60° C., and maintained at that temperature for 15 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and 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 2.50 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-3′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 37%).

Provenance & Evidence