Sodium Carbonate → 5-Chloro-2-(4-fluorophenyl)-1-(2-methylsulfinyl-4-pyrimidinyl)imdazo[4,5-b]pyridine

HRID 396371

Reaktionsgleichung

Reaktionsgleichung von HRID 396371
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CC(O)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:34])[N:12]=3)[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 224861505-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridine

Produkt 1

HCID 224861275-Chloro-2-(4-fluorophenyl)-1-(2-methylsulfinyl-4-pyrimidinyl)imdazo[4,5-b]pyridineAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21922555Acetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

5-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridine (372 mg 1 mmol) is dissolved in CH2Cl2/HOAc (7 ml 5/2) and treated with MCPBA (270 mg 70% 1.1 mmol) at 0° C. for 30 min. The reaction mixture is poured on 2N Na2CO3 and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered, evaporated to dryness and purified by SiO2 chromatography (ethyl acetate) to yield the title compound (400 mg 100%) as yellow foam.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by SiO2 chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-75eef910ccef439f8b5bda06d552cd72
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608072B1

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