Propanal → N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamine

HRID 1793077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793077
[Br:1][C:2]1[C:3]2[N:4]([C:9]([NH:14][CH2:15][CH2:16][CH3:17])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH:18](=O)[CH2:19][CH3:20].S(=O)(=O)(O)O.[BH4-].[Na+].[OH-].[Na+]>O1CCCC1.O>[Br:1][C:2]1[C:3]2[N:4]([C:9]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Komponenten

8

Edukt 5

HCID 527PropanalHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22024391N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine

Produkt 1

HCID 22024469N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylamineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine (103 mg) and propionaldehyde (57 mg) were dissolved in tetrahydrofuran (1.2 mL), then 3M sulfuric acid (0.24 mL) was added thereto, follwed by adding sodium borohydride (24 mg) under ice-cooling, and then the mixture was stirred for 3 hours. Water was added to the reaction mixture, which was neutralized with a 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9) to give the title compound (79 mg) as a white powder.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-714abe1a9d0f4f08a934c9727575f9bf
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078405B2

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