1,2-Dimethoxyethane → 1-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazole

HRID 420466Notes

Reaction equation

HRID 420466 reaction equation
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[CH3:17])=[CH:4][CH:3]=1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](B(O)O)=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[CH:33]2.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl>[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[N:10]=[C:9]3[CH3:17])=[CH:4][CH:3]=2)=[C:36]2[C:41]=1[CH:40]=[CH:39][CH:38]=[CH:37]2

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 152631321-(4-Bromophenyl)-2-methylbenzimidazoleHCID 2308855610-(2-Naphthyl)anthracene-9-boronic Acid

Product 1

HCID 577765421-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazoleYield 51.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolving 3.3 g (11 mmol) of 1-(4-bromophenyl)-2-methyl-1H-benzimidazole, 4.0 g (11 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.27 g of tetrakis (triphenylphosphine) palladium into 40 milliliter of 1,2-dimethoxyethane, adding 20 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloromethane, washed with water and dried with sodium sulfate. Removing the solvent by distillation and by refining the resultant product with the use of a silicagel column chromatography (dichloro methane-ethyl acetate), 2.9 g of yellowish white solids were obtained (yield: 49%). As a result of MS analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e=510 for molecular weight of 510.21.

Workup

  1. temperaturewith heating for 7 hours
  2. customAfter completion of the reaction
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. customRemoving the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-87463552b9e84561ba421c47037569f4
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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