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

HRID 1172764Notes

Reaction equation

HRID 1172764 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 66835618Tricyclohexylphosphine tolueneCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2efed5e28516491c8030e8c5bfbb8c71
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

Loading…