Ethyl bromoacetate → 8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester

HRID 500995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500995
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[C:10]([N:16]=[C:17](SC)[S:18][CH3:19])=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1.C(N(CC)CC)C>O>[CH2:6]([O:5][C:3]([C:2]1[N:11]2[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([Br:8])[C:10]2=[N:16][C:17]=1[S:18][CH3:19])=[O:4])[CH3:7]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 22024666methyl N-(3-bromo-5-methyl-2-pyridyl)(methylsulfanyl)methaneimidothioate

Produkt 1

HCID 684217148-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl bromoacetate (5.4 g) was added to methyl N-(3-bromo-5-methyl-2-pyridyl)-(methylsulfanyl)methaneimidothioate, and the mixture was stirred at 60° C. for 4 hours. After cooled to room temperature, triethylamine was added to treat the material, and water was further added thereto. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:9) to give 8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester (2.4 g) as a white powder.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. additionwas further added
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-31144bd7a59048e2bf80aaa8e7f65a5f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772249B2

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