2-Thiophenecarbonyl chloride → Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640890ノート

反応式

HRID 640890 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][CH:27]=1)[C:13]([C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1)=[O:14]>C1COCC1>[O:24]=[C:20]1[CH2:19][C:18]2[C:22](=[CH:23][C:15]([C:13]([C:12]3[CH:11]=[C:10]([NH:9][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[O:7])[CH:27]=[CH:26][CH:25]=3)=[O:14])=[CH:16][CH:17]=2)[NH:21]1

参加物

4

反応物 2

HCID 789282-Thiophenecarbonyl chlorideHCID 592564786-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

生成物 1

HCID 86610387Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A dry 250 mL flask was charged with Thiophene-2-carbonyl chloride (1.14 g, 7.77 mmol) and THF (60 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 1.508 g, 5.978 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 3 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was suspended in boiling EtOAc. The suspension was allowed to cool to room temperature before filtering to afford the Thiophene-2-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a tan solid (1.82 g, 5.02 mmol, 84%).

後処理

  1. temperatureto reflux for 3 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. temperatureto cool to room temperature
  5. filtrationbefore filtering

出典と根拠

ORDレコード
ord-c191d0ab587548069f0c993de6c35be6
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

反応ノート

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