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3,3-Dibromo-1,3-dihydro-1-((2-(trimethylsilyl)ethoxy)methyl)-2H-pyrrolo(2,3-b)pyridin-2-one → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

HRID 386615
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 386615
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:3]1=[O:19]>C1COCC1.[NH4+].[Cl-].[Zn]>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH2:2][C:3]1=[O:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 574588853,3-Dibromo-1,3-dihydro-1-((2-(trimethylsilyl)ethoxy)methyl)-2H-pyrrolo(2,3-b)pyridin-2-one

Produkt 1

HCID 574588861-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium Chloride
Lösungsmittel

Versuchsvorschrift

Zinc (100 g, 1.54 mol) was added to a solution of 3,3-dibromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (65 g, 0.154 mol) in THF (880 mL) and saturated aqueous NH4Cl (220 mL). After 3 h, the reaction mixture was filtered and concentrated in vacuo. The residue was partitioned between EtOAc and H2O which resulted in the formation of a white precipitate. Both layers were filtered through a Celite pad and the layers were separated. The aqueous layer was washed with EtOAc (2×500 mL) and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with CH2Cl2:EtOAc—90:10, to give the title compound. MS: m/z=265 (M+1).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc and H2O which
  4. customresulted in the formation of a white precipitate
  5. filtrationBoth layers were filtered through a Celite pad
  6. customthe layers were separated
  7. washThe aqueous layer was washed with EtOAc (2×500 mL)
  8. washthe combined organic layers were washed with H2O
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude product was purified by silica gel chromatography
  13. washeluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-35b87ee2c198445e9f02f78339799500
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372859B2

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