Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole

HRID 551037

Reaktionsgleichung

Reaktionsgleichung von HRID 551037
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 6764944-Bromoindole

Produkt 1

HCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromoindole (1.00 g, 5.10 mmol) in DMF (50 mL) at ambient temperature was added sodium hydride (220 mg of a 60% dispersion in mineral oil, 5.50 mmol). The reaction mixture was stirred for 5 min, then benzenesulfonyl chloride (901 mg, 5.10 mmol) was added and stirring was continued for 15 min. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with CHCl3 (2×75 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 90:10, to give the title compound. MS: m/z=336 (M+1).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 15 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
  4. extractionextracted with CHCl3 (2×75 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-c25a0b5ed9ed48e4afd66e9ad4ada2c4
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

Verknüpfte Notizen

Wird geladen…