Sodium hydride → 5-(2-chloropyridin-3-yl)-1-[(3-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde

HRID 1426667노트

반응식

HRID 1426667 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+].[F:17][C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([F:17])[CH:19]=3)(=[O:26])=[O:25])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 866239825-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

생성물 1

HCID 866239845-(2-chloropyridin-3-yl)-1-[(3-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde수율 95.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 5-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (250 mg) in tetrahydrofuran (25 mL) was added sodium hydride (60% in oil, 73 mg) at room temperature and the mixture was stirred for 15 min. 3-Fluorobenzenesulfonyl chloride (310 mg) was added to the reaction mixture, and the mixture was further stirred for 30 min. The reaction mixture was diluted with saturated brine, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a colorless oil (yield 420 mg, 95%).

후처리

  1. stirringthe mixture was further stirred for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-29c4c945c3cf4a29bbdcb0fdb9953bed
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933105B2

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