Toluene → 7-(3-Acetamidophenyl)-5-cyano-1-phenylbenzimidazole

HRID 644511Notes

Reaction equation

HRID 644511 reaction equation
[C:1]([C:3]1[CH:17]=[C:16](I)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].C1(C)C=CC=CC=1.[C:26]([NH:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>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.C(O)C>[C:26]([NH:29][C:30]1[CH:35]=[C:34]([C:16]2[C:6]3[N:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:8]=[N:9][C:5]=3[CH:4]=[C:3]([C:1]#[N:2])[CH:17]=2)[CH:33]=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 112450997-(3-Acetamidophenyl)-5-cyano-1-phenylbenzimidazoleYield 36.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

5-Cyano-7-iodo-1-phenylbenzimidazole (173 mg, 0.5 mmol), toluene (3.0 ml), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol), 3-acetamidophenylboronic acid (90 mg, 0.5 mmol), ethanol (3.0 ml) and potassium carbonate (138 mg, 1.0 mmol) were combined and the mixture was stirred at reflux overnight. The solvent was removed under reduced pressure and the crude product was purified on a 2 g silica Isolute® SPE column, eluting with dichloromethane/methanol (98:2). The eluent from this column was evaporated under reduced pressure and the crude product was purified further by prep LCMS, then recrystallised from dichloromethane/diethyl ether to give the product as a white solid (64 mg, 36%) m/z, 353.0 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified on a 2 g silica Isolute® SPE column
  4. washeluting with dichloromethane/methanol (98:2)
  5. customThe eluent from this column was evaporated under reduced pressure
  6. customthe crude product was purified further by prep LCMS
  7. customrecrystallised from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-cc8a7e9ea19e454386c55aa34271b616
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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