Sodium hydride → 1-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

HRID 1767544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767544
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]2[CH:11]=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1.[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Br>CN(C)C=O>[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][N:13]1[C:8]2[C:9](=[N:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH:11]=[CH:12]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridine

Produkt 1

HCID 178207361-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under argon and in an anhydrous medium, 590 mg (14.75 mmol) of sodium hydride (60% in oil) are added slowly to a solution of 1.81 g (12.23 mmol) of the compound obtained in Step B in 50 ml of N,N-dimethylformamide at 0° C. After 30 minutes' stirring at room temperature, 2.27 ml (14.75 mmol) of 2-bromobenzyl bromide in 15 ml of N,N-dimethylformamide are added dropwise to the reaction mixture. Stirring is maintained at room temperature under argon for two hours. After hydrolysis and then extraction with ethyl acetate, the organic phase is washed several times with water, dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 8:2) to yield the title compound in the form of a brown solid.

Aufarbeitung

  1. stirringStirring
  2. temperatureis maintained at room temperature under argon for two hours
  3. customAfter hydrolysis
  4. extractionextraction with ethyl acetate
  5. washthe organic phase is washed several times with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. custompurified by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-54c81279ba724d0bad9de79569b95559
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235550B2

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