Реакция #1994262

Уравнение реакции

potassium carbonate

10-(biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine

N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine

→

N-(biphenyl-4-yl)-N-(4-(10-(biphenyl-4-yl)-7-phenyl-9,10-dihydroacridin-2-yl)phenyl)biphenyl-4-amine

Выход 65.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONThen, distilled water (70 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Другоеpurified by silica gel
4. 4
   ЭкстракцияThen, a toluene layer was extracted
5. 5
   КонцентрированиеThe extracted organic solvent was concentrated
6. 6
   Другоеremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   Другоеto produce a solid
9. 9
   ФильтрацияThrough filtration
10. 10
    Другоеa yellowish brown solid was obtained
11. 11
    ДругоеIt was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

Методика

10-(biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridine (14 g, 28.6 mmol) was dissolved in toluene (500 mL) under a nitrogen atmosphere. Then, N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine (15 g, 28.6 mmol) was added thereto. To the resultant mixture solution, tetrakis triphenyl phosphine palladium (1.32 g, 1.14 mmol) and potassium carbonate (9.9 g, 71.5 mmol) were added. Then, distilled water (70 mL) was added thereto, followed by reflux-stirring for 4 hours. The resultant solution was cooled to about 60° C., and purified by silica gel. Then, a toluene layer was extracted. The extracted organic solvent was concentrated and removed, and methanol was added to produce a solid. Through filtration, a yellowish brown solid was obtained. It was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10)) to obtain N-(biphenyl-4-yl)-N-(4-(10-(biphenyl-4-yl)-7-phenyl-9,10-dihydroacridin-2-yl)phenyl)biphenyl-4-amine as a Cpd 14 compound (15 g, yield 65%, pale yellow solid).

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