Toluene → HCID 11472667, compound

HRID 644522Notes

Reaction equation

HRID 644522 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]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)#[N: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:1]([C:3]1[CH:17]=[C:16]([C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([C:26]#[N:27])[CH:33]=2)[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]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 11472667HCID 11472667, compoundYield 6%

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-cyanophenylboronic acid (73 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 (95:5). The eluent was concentrated under reduced pressure and the crude product was purified by reverse-phase prep LCMS to give the title compound (9.3 mg, 6%) m/z, 321.2 (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 (95:5)
  5. concentrationThe eluent was concentrated under reduced pressure
  6. customthe crude product was purified by reverse-phase prep LCMS

Sources & evidence

ORD record
ord-3cca519ed90b4c4f8b72be3d59fbb86d
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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