反応 #1994262

反応方程式

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

収率 65.0%

溶媒

toluene

反応条件

後処理

1. 1
   workup.DISTILLATIONThen, distilled water (70 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   その他purified by silica gel
4. 4
   抽出Then, a toluene layer was extracted
5. 5
   濃縮The extracted organic solvent was concentrated
6. 6
   その他removed
7. 7
   workup.ADDITIONmethanol was added
8. 8
   その他to produce a solid
9. 9
   ろ過Through filtration
10. 10
    その他a yellowish brown solid was obtained
11. 11
    その他It was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

実験手順

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).

出典