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

HRID 1907080Notes

Reaction equation

HRID 1907080 reaction equation
C1(C2C=CC=CC=2)C=CC([N:7]2[C:20]3[C:15](=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:18][CH:19]=3)[CH2:14][C:13]3[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]2=3)=CC=1.[C:34]1([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH:39]=[CH:38][C:37]([N:40](C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)[C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[CH:43][CH:42]=2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:17]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:19][C:20]([N:40]([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][C:50]4[N:7]([C:8]5[CH:9]=[CH:10][C:11]([C:8]6[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=6)=[CH:12][CH:13]=5)[C:20]5[C:15](=[CH:16][C:17]([C:21]6[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=6)=[CH:18][CH:19]=5)[CH2:14][C:49]=4[CH:48]=3)=[CH:43][CH:42]=2)[C:37]2[CH:36]=[CH:35][C:34]([C:68]3[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=3)=[CH:39][CH:38]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6752348010-(Biphenyl-4-yl)-2-bromo-7-phenyl-9,10-dihydroacridineHCID 67523594Bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine

Product 1

HCID 68007800N-(biphenyl-4-yl)-N-(4-(10-(biphenyl-4-yl)-7-phenyl-9,10-dihydroacridin-2-yl)phenyl)biphenyl-4-amineYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  1. distillationThen, distilled water (70 mL)
  2. additionwas added
  3. custompurified by silica gel
  4. extractionThen, a toluene layer was extracted
  5. concentrationThe extracted organic solvent was concentrated
  6. customremoved
  7. additionmethanol was added
  8. customto produce a solid
  9. filtrationThrough filtration
  10. customa yellowish brown solid was obtained
  11. customIt was purified through silica gel column chromatography (methylene chloride/n-hexane (1/10))

Sources & evidence

ORD record
ord-2b3c87de96884a5facb3487e75872448
Source dataset
uspto-grants-2013_12
Patent number
US08597802B2

Reaction notes

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