تفاعل #1994262

معادلة التفاعل

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

المردود 65.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONThen, distilled water (70 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   أخرىpurified by silica gel
4. 4
   استخلاصThen, a toluene layer was extracted
5. 5
   تركيزThe extracted organic solvent was concentrated
6. 6
   أخرىremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   أخرىto produce a solid
9. 9
   ترشيحThrough filtration
10. 10
    أخرىa yellowish brown solid was obtained
11. 11
    أخرىIt was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

الإجراء التجريبي

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).

المصدر