Methyl Acrylate → HCID 67485840, compound

HRID 644533Notes

Reaction equation

HRID 644533 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[C:7]([C:9]1[CH:23]=[C:22](I)[C:12]2[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=[N:15][C:11]=2[CH:10]=1)#[N:8].C(N(CC)CC)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:22]1[C:12]2[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=[N:15][C:11]=2[CH:10]=[C:9]([C:7]#[N:8])[CH:23]=1

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 674856275-Cyano-7-iodo-1-phenylbenzimidazole

Product 1

HCID 67485840HCID 67485840, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 6342AcetonitrileSolvent

Procedure

Methyl acrylate (0.27 ml, 3 mmol), 5-cyano-7-iodo-1-phenylbenzimidazole (346 mg, 1.0 mmol), triethylamine (0.28 ml, 2 mmol) palladium acetate (4.5 mg, 0.02 mmol), tri-o-tolylphosphine (16.1 mg, 0.05 mmol) and acetonitrile (5 ml) were combined in Reactivial™. The mixture was heated under 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 (250 mg, 83%), m/z 304.2 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder 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-732b2da378444f94914f5e5fc2b6cbfd
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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