Sodium Carbonate → 1-[4-(9,10-diphenylanthracen-2-yl)phenyl]-2-phenyl-1H-benzimidazole

HRID 1172775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172775
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[C:23]1([C:29]2[C:30]3[C:35]([C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:37]4[C:42]=2[CH:41]=[C:40](B(O)O)[CH:39]=[CH:38]4)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[C:23]1([C:29]2[C:30]3[C:35]([C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:37]4[C:42]=2[CH:41]=[C:40]([C:2]2[CH:3]=[CH:4][C:5]([N:8]5[C:12]6[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=6[N:10]=[C:9]5[C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:6][CH:7]=2)[CH:39]=[CH:38]4)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Produkt 1

HCID 589538151-[4-(9,10-diphenylanthracen-2-yl)phenyl]-2-phenyl-1H-benzimidazoleAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.2 g (3.2 mmol) of 9,10-diphenylanthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1.6 g of a greenish white solid (90% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 598 with respect to a molecular weight of 598.24.

Aufarbeitung

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. washthe resultant solid was washed with water, methanol, and toluene

Quellen und Nachweise

ORD-Eintrag
ord-814ada64fb4847f18afe8b2ec7b2dc3e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833632B2

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