Sodium hydride → 5-Bromo-1-(methylsulfonyl)indoline

HRID 2280618

Reaktionsgleichung

Reaktionsgleichung von HRID 2280618
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:14]([CH3:13])(=[O:16])=[O:15])[CH2:8][CH2:7]2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 34115665-Bromoindoline

Produkt 1

HCID 5759865-Bromo-1-(methylsulfonyl)indolineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To DMF (5.0 ml) was added sodium hydride (53 mg, 1.3 mmol) and the solution stirred at room temperature for 30 min. 5-Bromoindoline (240 mg, 1.2 mmol) was added and the solution was stirred at room temperature for 30 min. Methanesulfonyl chloride (94 ul, 1.2 mmol) was added and the solution stirred at room temperature overnight, then concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 2% CH3OH/CHCl3 to give the title compound (202 mg, 60%).

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for 30 min
  2. stirringthe solution stirred at room temperature overnight
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel eluting with 2% CH3OH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-3b045b00fe384555aa053864354c64ad
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139536B2

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