反应详情

In a stream of argon, 0.714 g (3.22 mmol) of 9-phenanthreneboronic acid, 1.50 g (3.22 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine and 37.2 mg (0.0322 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 120 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 50° C. To the suspension, 9.66 mL (9.66 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. Then the mixture was cooled to room temperature, and 0.961 g (4.83 mmol) of 4-(2-pyridyl)phenylboronic acid and 9.66 mL (9.66 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 1.28 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4′-(2-pyridyl)biphenyl-3-yl]-pyrimidine as a white solid (yield: 62%).

1. temperatureThen the mixture was heated to 60° C.
2. temperaturemaintained at that temperature for 4 hours
3. stirringwhile being stirred
4. temperatureThen the reaction mixture was cooled to room temperature
5. distillationwas then distilled under a reduced pressure
6. customto remove all volatile materials
7. additionMethanol was added to the concentrate
8. filtrationthe thus-deposited solid was collected by filtration
9. customThe obtained crude product
10. customwas purified by silica gel chromatography
11. additionmixed solvent as an eluent