2-Aminopyridine → HCID 24738180, Verbindung

HRID 731608

Reaktionsgleichung

Reaktionsgleichung von HRID 731608
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:10][C:9]1[O:8][N:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]=1[C:3]1[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]2[CH:2]=1

Komponenten

5

Edukt 3

HCID 104392-Aminopyridine2×HCID 516892Sodium BicarbonateHCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

Produkt 1

HCID 24738180HCID 24738180, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (140 mg, 0.5 mmol) and 2-aminopyridine (47 mg, 0.5 mmol) in ethanol (3.1 mL) was heated under reflux under argon for 3.5 h. Then another portion of 2-aminopyridine (24 mg, 0.25 mmol) was added and heating under reflux continued for another 1 h. The resulting mixture was then cooled to room temperature and then sodium hydrogen carbonate (63 mg, 0.75 mmol) added and the resulting mixture heated under reflux for 2 h. After cooling to room temperature, the mixture was poured onto water and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (76 mg, 55%) which was obtained as a light yellow gum. MS: m/e=276.0 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux under argon for 3.5 h
  3. temperatureheating
  4. temperatureunder reflux
  5. temperaturethe resulting mixture heated
  6. temperatureunder reflux for 2 h
  7. temperatureAfter cooling to room temperature
  8. additionthe mixture was poured onto water
  9. extractionextracted with ethyl acetate
  10. washThe combined organic layers were then washed with water and brine
  11. dry with materialdried over sodium sulphate
  12. customevaporated
  13. customto leave a yellow oil
  14. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-696ff80f9aef4bb98014deb962024899
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585874B2

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