Toluene → 3-{10-[4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9-anthryl}pyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

In a 100 mL three-necked flask were placed 0.66 g (2.0 mmol) of 3-(10-bromo-9-anthryl)pyridine, 0.63 g (2.4 mmol) of 4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylboronic acid, 0.45 g (4.0 mmol) of sodium carbonate, 25 mL of toluene, 3 mL of water, and 6 mL of ethanol. The mixture was degassed by being stirred under reduced pressure, and the atmosphere in the flask was replaced with nitrogen. To this mixture was added 58 mg (0.050 mmol) of tetrakis(triphenylphosphine)palladium(0), and the resulting mixture was refluxed under a nitrogen stream at 120° C. for 23 hours. After a predetermined time has passed, water was added to this mixture, and the aqueous layer was extracted with ethyl acetate. The obtained extract and the organic layer were combined and washed with saturated brine, and then the organic layer was dried with magnesium sulfate. The obtained mixture was subjected to gravity filtration, and the resulting filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (a 5:1 ratio of toluene to ethyl acetate). Recrystallization from a mixed solvent of toluene and hexane gave 0.65 g of a solid in 69% yield, which was the desired substance.

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