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Sodium hydride → 3-{[2-(2-chloropyridin-3-yl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile

HRID 1426726
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HRID 1426726 반응식
[Cl:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[C:17]([C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)#[N:18]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:25]([C:21]3[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=3)[C:17]#[N:18])(=[O:27])=[O:26])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 866239825-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

생성물 1

HCID 866239983-{[2-(2-chloropyridin-3-yl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile수율 76%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 516892
Sodium Bicarbonate
용매

실험 절차

To a solution of 5-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (110 mg) in tetrahydrofuran (11 mL) was added sodium hydride (60% in oil, 64 mg) at room temperature and the mixture was stirred for 10 min. 3-Cyanobenzenesulfonyl chloride (215 mg) was added and the mixture was further stirred for 15 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound as colorless crystals (yield 150 mg, 76%).

후처리

  1. stirringthe mixture was further stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. extractionThe obtained extract
  4. washwas washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-2fb299da3c0f4b52a5ac489ccbebded6
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933105B2

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