Sodium Carbonate → Biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-[4-(8,8-diphenyl-8H-indolo[3,2,1-de]acridin-3-yl)phenyl]amine

HRID 2277361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277361
[C:1]1([C:7]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]3[C:15]4=[C:16]([C:21]5[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=5[N:14]4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=4)[CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]1([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:41]=[CH:40][C:39]([N:42]([C:58]2[CH:63]=[CH:62][C:61](Br)=[CH:60][CH:59]=2)[C:43]2[CH:55]=[CH:54][C:53]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:46]([CH3:57])([CH3:56])[C:45]=3[CH:44]=2)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.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.O>[C:36]1([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:37]=[CH:38][C:39]([N:42]([C:43]2[CH:55]=[CH:54][C:53]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:46]([CH3:57])([CH3:56])[C:45]=3[CH:44]=2)[C:58]2[CH:63]=[CH:62][C:61]([C:23]3[CH:24]=[CH:25][C:26]4[N:14]5[C:13]6[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=6[C:7]([C:30]6[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=6)([C:1]6[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=6)[C:20]6[C:15]5=[C:16]([CH:17]=[CH:18][CH:19]=6)[C:21]=4[CH:22]=3)=[CH:60][CH:59]=2)=[CH:40][CH:41]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58131689N-((1,1'-Biphenyl)-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amineHCID 681691638,8-diphenyl-8H-indolo[3,2,1-de]acridine-3-boronic acid

Produkt 1

HCID 67324655Biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)-[4-(8,8-diphenyl-8H-indolo[3,2,1-de]acridin-3-yl)phenyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

85 g (190 mmol) of 8,8-diphenyl-8H-indolo[3,2,1-de]acridine-3-boronic acid, 98 g (190 mmol) of biphenyl-4-yl-(4-bromophenyl)-(9,9-dimethyl-9H-fluoren-2-yl)amine and 13 g (123 mmol) of sodium carbonate are suspended in 180 ml of toluene, 180 ml of dioxane and 60 ml of water. 3.0 mg mmol) of Pd(PPh3)4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum. The purity is 99.9%. The yield is 124 g (147 mmol), corresponding to 78% of theory.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-00d8f3eaf326453eb5cfab3a287d2a2b
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133119B2

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