Potassium Phosphate, Tribasic → 1-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

HRID 2371241Notes

Reaction equation

HRID 2371241 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:45]1[C:62]2[C:61]3[C:60]4[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=4[CH:54]=[CH:53][C:52]=3[CH:51]=[C:50](B(O)O)[C:49]=2[CH:48]=[CH:47][CH:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[C:42]([C:48]3[C:49]4[CH:50]=[CH:51][C:52]5[CH:53]=[CH:54][C:55]6[CH:56]=[CH:57][CH:58]=[CH:59][C:60]=6[C:61]=5[C:62]=4[CH:45]=[CH:46][CH:47]=3)[CH:41]=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleHCID 59622711Benzo[c]phenanthren-5-ylboronic acid

Product 1

HCID 866595461-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a vigorously stirred suspension of 17.5 g (50 mmol) of 1-phenyl-2-(4-bromophenyl)benzimidazole, 14.9 g (55 mmol) of benzo[c]phenanthrene-5-boronic acid and 25.5 g (120 mmol) of tripotassium phosphate in a mixture of 300 ml of toluene, 100 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After the mixture has been cooled, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and recrystallised three times from DMF (about 7 ml/g). Yield: 16.8 g (34 mmol), 67.8%, purity 99.9% (HPLC).

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter the mixture has been cooled
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 7 ml/g)

Sources & evidence

ORD record
ord-005daff99dc74fc7bd2c56d5a2f89346
Source dataset
uspto-grants-2014_04
Patent number
US08710284B2

Reaction notes

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