Toluene → HCID 11256251, compound

HRID 644517Notes

Reaction equation

HRID 644517 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.[CH3:26][N:27]([CH3:37])[C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=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:32]2[CH:31]=[CH:30][CH:29]=[C:28]([N:27]([CH3:37])[CH3:26])[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 27625273-(Dimethylamino)benzeneboronic acidHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 11256251HCID 11256251, compoundYield 38%

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-dimethylaminophenylboronic acid (82 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 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 Recrystallisation from diethyl ether afforded the title compound (64 mg, 38%) m/z, 339.0 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under reduced pressure and crude product
  3. customwas 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
  8. customthe product Recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-73abf80525ec465bb91814dcbe938525
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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