6-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester → 4-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamide

HRID 1355659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355659
C(OC([C:8]1(C(OC(C)(C)C)=O)[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:30])(=[O:29])[N:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=2)[C:9]1=[O:31])=O)(C)(C)C>FC(F)(F)C(O)=O>[Br:17][C:13]1[CH:12]=[C:11]2[C:16]([CH2:8][C:9](=[O:31])[N:10]2[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([N:26]([CH3:27])[CH3:28])(=[O:30])=[O:29])=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Komponenten

3

Edukt 1

HCID 700321706-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester

Produkt 1

HCID 185077814-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamideAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

6-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester (10.0 g, 16.4 mmol) was dissolved in 50 ml of trifluoroacetic acid (TFA) under an atmosphere of dry N2 and stirred overnight at ambient temperature. The reaction mixture was then concentrated under vacuum and partitioned between DCM and saturated aqueous sodium bicarbonate (NaHCO3). The DCM layer was then dried over MgSO4, filtered and concentrated under vacuum to give 6.05 g of the titled compound as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. custompartitioned between DCM and saturated aqueous sodium bicarbonate (NaHCO3)
  3. dry with materialThe DCM layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-de43736401324176ab63ee47d4daa473
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586447B1

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