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tert-Butyl mercaptan → 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 533601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 533601
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].[H-].[Na+].F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:27]([CH3:28])[C:18]2=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=[C:17]2[N:16]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:2]([S:5][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:27]([CH3:28])[C:18]2=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:22]=[C:17]2[N:16]=1)([CH3:4])([CH3:3])[CH3:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 679818402-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Produkt 1

HCID 867081972-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of tert-butylthiol (0.67 g) and DMF (12 ml), sodium hydride (60% in oil) was added under ice-cooling. The mixture was stirred under ice-cooling for 10 minutes, and then 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.09 g) was added. The mixture was stirred at room temperature for 1 hour, and then stirred with heating at 60° C. for 1.5 hours, then at 80° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.19 g of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 15).

Aufarbeitung

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling for 10 minutes
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. stirringstirred
  6. temperatureInto the reaction mixture cooled to room temperature
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7ac5df42268d47ab851013dad137c3c3
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853238B2

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