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

HRID 420464Notes

Reaction equation

HRID 420464 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[C:17]2C=CC=CN=2)=[CH:4][CH:3]=1.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40](B(O)O)=[C:39]2[C:34]=1[CH:35]=[CH:36][CH:37]=[CH:38]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:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]([C:2]2[CH:3]=[CH:4][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:6][CH:7]=2)=[C:41]2[C:46]=1[CH:45]=[CH:44][CH:43]=[CH:42]2

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2308855610-(2-Naphthyl)anthracene-9-boronic AcidHCID 230940571-(4-Bromophenyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole

Product 1

HCID 577765421-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazoleYield 69.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolving 1.2 g (3.4 mmol) of 1-(4-bromophenyl)-2-pyridine-2-yl-1H-benzimidazole, 1.2 g (3.4 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.10 g of tetrakis (triphenylphosphine) palladium into 15 milliliter of 1,2-dimethoxyethane, adding 6 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), 1.2 g of an yellowish white solids were obtained (yield: 61%). As a result of MS analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e=573 for molecular weight of 573.22.

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-a47570c8e78d4503a532690758bebbc3
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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