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

HRID 2262437Notes

Reaction equation

HRID 2262437 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 dichloro-methane, 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-1109adea6cea445e972a3703bf9bc300
Source dataset
uspto-grants-2010_12
Patent number
US07851071B2

Reaction notes

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