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

HRID 1426667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426667
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 866239845-(2-chloropyridin-3-yl)-1-[(3-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehydeAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-29c4c945c3cf4a29bbdcb0fdb9953bed
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933105B2

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