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

Participants

Reaction Steps

In a stream of argon, 1.91 g (8.56 mmol) of 9-phenanthreneboronic acid, 4.00 g (8.56 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 98.9 mg (0.086 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 320 mL of toluene and 40 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 25.7 mL (25.7 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 4 hours. Then the mixture was cooled to room temperature, and 2.56 g (12.8 mmol) of 4-(2-pyridyl)phenylboronic acid and 25.7 mL (25.7 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 70° C. and maintained at that temperature for 12 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 3.91 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4′-(2-pyridyl)biphenyl-3-yl]-1,3,5-triazine as a white solid (yield: 64%).

Provenance & Evidence