Cesium carbonate → HCID 86614800, compound

HRID 1172766Notes

Reaction equation

HRID 1172766 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.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[C:39]1[C:40]2[C:45]([C:46]([C:56]3[CH:65]=[CH:64][C:63]4[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:57]=3)=[C:47]3[C:52]=1[CH:51]=[C:50](B(O)O)[CH:49]=[CH:48]3)=[CH:44][CH:43]=[CH:42][CH:41]=2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:72]1(P(C2CCCCC2)C2CCCCC2)[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]1.C1(C)C=CC=CC=1>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].O1CCOCC1>[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:42]5[CH:43]=[CH:44][C:45]6[C:40](=[C:39]([C:30]7[CH:31]=[CH:32][C:33]8[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=8)[CH:29]=7)[C:52]7[C:47]([C:46]=6[C:56]6[CH:65]=[CH:64][C:63]8[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=8)[CH:57]=6)=[CH:48][CH:49]=[CH:50][CH:51]=7)[C:41]=5[C:72]5[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=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 23160220[9,10-Di(naphthalen-2-yl)anthracen-2-yl]boronic acidHCID 231602311h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-HCID 66835618Tricyclohexylphosphine toluene

Product 1

HCID 86614800HCID 86614800, compoundYield 874.4%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2.3 g (6.0 mmol) of 5-(4-chlorophenyl)-1,2-diphenyl-1H-benzimidazole, 3.1 g (6.6 mmol) of 9,10-di(2-naphthyl)anthracene-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 3.2 g of a greenish white solid (69% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 774 with respect to a molecular weight of 774.30.

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-5d794da6d55a42d5bc19c19040fb75dc
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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