Toluene → HCID 11449329, compound

HRID 644519Notes

Reaction equation

HRID 644519 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.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.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:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=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 2734379(Pyridin-4-yl)boronic acidHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 11449329HCID 11449329, compoundYield 32.4%

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), pyridin-4-yl boronic acid (62 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 suspended in acetonitrile then treated with diethyl ether to precipitate the product. The mother liquors were removed by filtration and the residual solid was further purified on a Biotage silica gel cartridge, eluting with dichloromethane/methanol (98:2). Recrystallisation from dichloromethane/diethyl ether afforded the title compound (48 mg, 32%) m/z, 297.4 (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. additionthen treated with diethyl ether
  7. customto precipitate the product
  8. customThe mother liquors were removed by filtration
  9. customthe residual solid was further purified on a Biotage silica gel cartridge
  10. washeluting with dichloromethane/methanol (98:2)
  11. customRecrystallisation from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-a2c67b797d804019a9f665386a9463c1
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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