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

HRID 640890노트

반응식

HRID 640890 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c191d0ab587548069f0c993de6c35be6
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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