Sodium Carbonate → 2-[4-[10-(2-Naphthalenyl)-9-anthracenyl]phenyl]-1-phenyl-1H-benzimidazole

HRID 420454Notes

Reaction equation

HRID 420454 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=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.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.COCCOC>[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]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:11]4[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=4[N:9]=3)=[CH:4][CH:3]=2)=[C:39]2[C:34]=1[CH:35]=[CH:36][CH:37]=[CH:38]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2308855610-(2-Naphthyl)anthracene-9-boronic AcidHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

Product 1

HCID 591672632-[4-[10-(2-Naphthalenyl)-9-anthracenyl]phenyl]-1-phenyl-1H-benzimidazoleYield 81%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolving 4.0 g (11 mmol) of 2-(4-bromophenyl)-1-phenyl-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 18 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 5.1 g of yellowish white solids (yield: 78%). As a result of mass spectrum (MS) analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e=572 for molecular weight of 572.23.

Workup

  1. temperaturewith heating for 7 hours
  2. customAfter completion of the reaction, separation
  3. filtrationwith filtration
  4. washresultant crystals were washed with water and methanol

Sources & evidence

ORD record
ord-cae517e831e54f0480835bd6d8906f8f
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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