Water → 9-tert-butyl-3-methoxy-2-bromo-14-chloro-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971735
[C:1]([N:5]1[CH2:26][CH2:25][CH2:24][CH2:23][C:8]2[CH:9]=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[Cl:28]N1C(=O)CCC1=O.O>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[C:1]([N:5]1[CH2:26][CH2:25][CH2:24][CH2:23][C:8]2[C:9]([Cl:28])=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:27])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 58124845HCID 58124845, Verbindung

Produkt 1

HCID 581249549-tert-butyl-3-methoxy-2-bromo-14-chloro-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-oneAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24477Sodium ThiosulfateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 66 mg of 19d in 1 ml of DMF was added at 0° C. 27 mg of N-chlorosuccinimide. The mixture was stirred for 2 h. Then, 5 ml of water was added and 1 drop of a sat. Na2S2O3 solution. Stirring was continued for 5 min and the product was extracted into ethyl acetate. The extract was washed with water, dried, concentrated and the residue was treated with cold pentane, to provide 65 mg of 19e as a white crystalline material; Mp 203-205° C. MS-ESI: [M+1] 464.12, 465.10, 466.09, 467.08, 468.08 and 469.07.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 5 min
  3. extractionthe product was extracted into ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionthe residue was treated with cold pentane

Quellen und Nachweise

ORD-Eintrag
ord-e3f9961a01af4a5ea07992c330566ff2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431564B2

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