Reaktion #1994262

Reaktionsgleichung

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

Ausbeute 65.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThen, distilled water (70 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigepurified by silica gel
4. 4
   ExtraktionThen, a toluene layer was extracted
5. 5
   EinengenThe extracted organic solvent was concentrated
6. 6
   Sonstigeremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   Sonstigeto produce a solid
9. 9
   FiltrationThrough filtration
10. 10
    Sonstigea yellowish brown solid was obtained
11. 11
    SonstigeIt was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

Vorschrift

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).

Quelle