Water → 5-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

HRID 927568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927568
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].IC.[C:18](=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:18][O:14][C:13]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([O:8][CH2:9][CH2:10][O:11][CH3:12])[N:6]=1)=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 710877515-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid

Produkt 1

HCID 710877995-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl esterAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid (2.48 g, 9 mmol), iodomethane (2.55 g, 18 mmol) and sodium carbonate (0.106 g, 9 mmol) in DMF (30 mL) was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed three times with brine, dried (sodium sulfate) and evaporated. The residue was purified by column chromatography (silica gel, 50 g, 30% ethyl acetate in petroleum ether) to yield the title compound (1.7 g, 6 mmol, 65%) as yellow solid; MS (EI): m/e 290.0 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed three times with brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel, 50 g, 30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-a956b357f569416682e078cbb78387db
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290451B2

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