Nitrogen → 2-[4-(10-Phenanthren-3-ylanthracen-9-yl)phenyl]-1-phenyl-1h-benzimidazole

HRID 879925Notes

Reaction equation

HRID 879925 reaction equation
BrC1[C:3]2[C:8]([C:9]([C:16]3[CH:17]=CC4C=CC5C(C=4[CH:29]=3)=CC=CC=5)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:30]1([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=[C:37]2C2C=CC(B(O)O)=CC=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+].N#N.[C:62]1([CH3:68])[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CO>[CH:64]1[C:65]2[CH:10]=[CH:9][C:8]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:66]=2[CH:67]=[C:62]([C:68]2[C:17]3[C:16](=[CH:29][CH:11]=[CH:12][CH:13]=3)[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:37]4[N:36]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[N:38]=4)=[CH:14][CH:15]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)[CH:63]=1

Participants

9

Reactant 5

HCID 947NitrogenHCID 1140TolueneHCID 10340Sodium CarbonateHCID 532497794-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic AcidHCID 596295449-Bromo-10-phenanthren-3-ylanthracene

Product 1

HCID 596295792-[4-(10-Phenanthren-3-ylanthracen-9-yl)phenyl]-1-phenyl-1h-benzimidazoleYield 68%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

32 g (70 mmol) of 9-bromo-10-phenanthren-3-ylanthracene, 26.3 g (84 mmol) of 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid and 125 ml of 2 M Na2CO3 solution are suspended in 500 ml of toluene and 500 ml of EtOH, the mixture is saturated with N2, 1.7 g (1.8 mmol) of tetrakis(triphenylphosphine)palladium(0) are added, and the mixture is heated at the boil for 2 h. The mixture is poured into 1.5 l of a mixture of water/MeOH/6 M HCl 1:1:1, and the yellow precipitate is filtered off with suction, washed with water, EtOH and toluene and dried. Subsequent Soxhlet extraction with chloroform, removal of the solvent, recrystallisation three times from toluene and sublimation twice in vacuo (p=1×10−5 mbar, T=385° C.) give 30 g (68%) of a pale-yellow powder having a purity of >99.9% (HPLC).

Workup

  1. additionare added
  2. temperaturethe mixture is heated at the boil for 2 h
  3. filtrationthe yellow precipitate is filtered off with suction
  4. washwashed with water, EtOH and toluene
  5. customdried
  6. extractionSubsequent Soxhlet extraction
  7. customwith chloroform, removal of the solvent, recrystallisation three times from toluene and sublimation twice in vacuo (p=1×10−5 mbar, T=385° C.)

Sources & evidence

ORD record
ord-ab83d728c9b84a7caab39f2bdb2bb0db
Source dataset
uspto-grants-2015_03
Patent number
US08993123B2

Reaction notes

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