Toluene → HCID 11313772, compound

HRID 644518Notes

Reaction equation

HRID 644518 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.[CH2:26]1[O:34][C:33]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][C:28]=2[O: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:31]2[CH:30]=[CH:29][C:28]3[O:27][CH2:26][O:34][C:33]=3[CH:32]=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 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 11313772HCID 11313772, compound

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), 3,4-methylene dioxyphenylboronic acid (83 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 product was crystallised from dichloromethane/diethyl ether to the title compound (75 mg, 44%) m/z, 339.8 (M+H)+.

Workup

  1. temperatureat reflux overnight The solvent
  2. customwas 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 and product
  6. customwas crystallised from dichloromethane/diethyl ether to the title compound (75 mg, 44%) m/z, 339.8 (M+H)+

Sources & evidence

ORD record
ord-03e2881238c64304bd6f19f28ae08ada
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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