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

HRID 644532
ノート
印刷プレビュー

反応式

HRID 644532 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒
HCID 167845
palladium(II) acetate
触媒
HCID 6342Acetonitrile溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-900f3a91462240daaa37ac110157b171
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700638B2

反応ノート

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