Methyl Acrylate → 3-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl ester

HRID 644532Notes

Reaction equation

HRID 644532 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].I[C:8]1[C:13]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=[N:16][C:12]=2[CH:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][C:8]1[C:13]2[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=[N:16][C:12]=2[CH:11]=[C:10]([C:23]([F:25])([F:26])[F:24])[CH:9]=1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 674849573-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl esterYield 92.4%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Methyl acrylate (2.7 ml, 30 mmol), 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (3.48 g, 10 mmol), triethylamine (2.79 ml, 20 mmol), palladium acetate (45 mg, 0.2 mmol), tri-o-tolylphosphine (161 mg, 0.53 mmol) and acetonitrile (50 ml) were combined and the mixture heated at reflux under an argon atmosphere for 17 h. The mixture was cooled, filtered through Dicalite and the filtrate was concentrated under reduced pressure. Crystals formed and were isolated by filtration and dried to give the title compound (3.2 g, 92%), m/z 347.0 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under an argon atmosphere for 17 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through Dicalite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customCrystals formed
  7. customwere isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-900f3a91462240daaa37ac110157b171
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

Loading…