Potassium Carbonate → 10-(Biphenyl-4-yl)-7-[4-bis(biphenyl-4-yl)amino-phenyl]-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole

HRID 719054

Reaktionsgleichung

Reaktionsgleichung von HRID 719054
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([CH:7]2[CH:26]=[C:25]3[C:10](=[C:11](Br)[C:12]4[CH:13]=[C:14]5[C:22]([C:23]([CH3:28])([CH3:27])[C:24]=43)=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]3)=[N:15]5)[CH:9]=[CH:8]2)=[CH:3][CH:2]=1.[C:36]1([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:41]=[CH:40][C:39]([N:42]([C:58]2[CH:63]=[CH:62][C:61]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[CH:60][CH:59]=2)[C:43]2[CH:48]=[CH:47][C:46](B3OC(C)(C)C(C)(C)O3)=[CH:45][CH:44]=2)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([CH:7]2[CH:26]=[C:25]3[C:10](=[C:11]([C:46]4[CH:45]=[CH:44][C:43]([N:42]([C:58]5[CH:59]=[CH:60][C:61]([C:64]6[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=6)=[CH:62][CH:63]=5)[C:39]5[CH:40]=[CH:41][C:36]([C:70]6[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=6)=[CH:37][CH:38]=5)=[CH:48][CH:47]=4)[C:12]4[CH:13]=[C:14]5[C:22]([C:23]([CH3:28])([CH3:27])[C:24]=43)=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]3)=[N:15]5)[CH:9]=[CH:8]2)=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 67523594Bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amineHCID 8668501710-(Biphenyl-4-yl)-7-bromo-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole

Produkt 1

HCID 8668501910-(Biphenyl-4-yl)-7-[4-bis(biphenyl-4-yl)amino-phenyl]-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazoleAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
73 °C

Versuchsvorschrift

10-(biphenyl-4-yl)-7-bromo-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole synthesized in Example 6 (13.0 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine (15.9 g) a toluene/ethanol (4/1, v/v) mixed solvent (250 ml), and a 2M potassium carbonate aqueous solution (51 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (2.1 g), and stirred at 73° C. for 10 hours. After the mixture was cooled to a room temperature, a precipitated crude product was collected by filtration. 1,2-Dichlorobenzene (1.7 L) was added to the crude product, and the crude product was dissolved while being heated, and after removing insoluble matter by filtration, a filtrate was cooled to a room temperature. A precipitated solid was collected by filtration and purified by recrystallization using 1,2-dichlorobenzene (1.7 L) to obtain a white powder of 10-(biphenyl-4-yl)-7-[4-bis(biphenyl-4-yl)amino-phenyl]-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole (13.4 g; yield 63.8%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureAfter the mixture was cooled to a room temperature
  3. customa precipitated crude product
  4. filtrationwas collected by filtration
  5. addition1,2-Dichlorobenzene (1.7 L) was added to the crude product
  6. dissolutionthe crude product was dissolved
  7. temperaturewhile being heated
  8. customafter removing insoluble matter
  9. filtrationby filtration
  10. temperaturea filtrate was cooled to a room temperature
  11. filtrationA precipitated solid was collected by filtration
  12. custompurified by recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-07f54a355aab47bb85b9085cb929a77b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09196837B2

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