Cesium carbonate → 1,2-diphenyl-5-[4-(9,10-diphenylanthracen-2-yl)phenyl]-1H-benzimidazole

HRID 1172764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172764
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:28]=[CH:27][C:11]3[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[C:29]1([C:35]2[C:36]3[C:41]([C:42]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[C:43]4[C:48]=2[CH:47]=[C:46](B(O)O)[CH:45]=[CH:44]4)=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1>[C:21]1([N:12]2[C:11]3[CH:27]=[CH:28][C:8]([C:5]4[CH:6]=[CH:7][C:2]([C:39]5[CH:38]=[CH:37][C:36]6[C:41](=[C:42]([C:52]7[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=7)[C:43]7[C:48]([C:35]=6[C:29]6[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=6)=[CH:47][CH:46]=[CH:45][CH:44]=7)[CH:40]=5)=[CH:3][CH:4]=4)=[CH:9][C:10]=3[N:14]=[C:13]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 231602159,10-Diphenylanthracene-2-boronic AcidHCID 231602311h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-

Produkt 1

HCID 231602161,2-diphenyl-5-[4-(9,10-diphenylanthracen-2-yl)phenyl]-1H-benzimidazoleAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 66835618Tricyclohexylphosphine tolueneKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.3 g (6.0 mmol) of 5-(4-chlorophenyl)-1,2-diphenyl-1H-benzimidazole, 2.5 g (6.6 mmol) of 9,10-diphenylanthracene-2-boronic acid, tris(dibenzylideneacetone)dipalladium (0) (0.14 g, 0.15 mmol), and cesium carbonate (4.7 g, 14 mmol) were suspended into 20 mL of anhydrous dioxane, a solution of tricyclohexylphosphine/toluene (25 mass %, 0.49 ml, 0.43 mmol) was added, and the whole was stirred at 80° C. for 10 hours. The reaction mixture was diluted with 200 mL of toluene and 100 mL of water, and was filtered through Celite 545 for removing Pd black. An organic layer was fractionated from the filtrate, washed with 50 mL of a saturated sodium chloride solution, and dried with anhydrous magnesium sulfate, and the solvent was distilled off, with the result that red oil was obtained. The oil was purified by means of silica gel column chromatography to obtain 3.0 g of a greenish white solid (75% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 674 with respect to a molecular weight of 674.27.

Aufarbeitung

  1. filtrationwas filtered through Celite 545
  2. customfor removing Pd black
  3. washwashed with 50 mL of a saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customwith the result that red oil
  7. customwas obtained
  8. customThe oil was purified by means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2efed5e28516491c8030e8c5bfbb8c71
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833632B2

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