Triethylamine → 2-Bromo-4-(5-methyl-3-phenyl-isoxazol-4-yl)-pyridine

HRID 1375639

Reaktionsgleichung

Reaktionsgleichung von HRID 1375639
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[C:19](=[N:27]O)(Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:27][O:11][C:9]=2[CH3:10])[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2756315N-hydroxybenzenecarboximidoyl chlorideHCID 234356431-(2-Bromopyridin-4-yl)propan-2-one

Produkt 1

HCID 234356652-Bromo-4-(5-methyl-3-phenyl-isoxazol-4-yl)-pyridineAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of Compound 16 (1.71 g, 8.0 mmol) and Et3N (2.23 mL, 16 mmol) in EtOH (16 mL) was added a solution of benzoylchloride oxime (1.62 g, 10.4 mmol) in EtOH (16 mL) over 90 min. The solution was stirred at 25° C. for 90 min. Then, the solution was heated to reflux for 24 h. The solution was cooled to 25° C. and concentrated. The crude material was taken up in CH2Cl2 (50 mL) and poured into saturated aqueous NaHCO3 (50 mL), extracted with CH2Cl2 (3×50 mL), dried (Na2SO4), and filtered. Flash chromatography (SiO2, 20% EtOAc-hexanes) provided the title compound (1.32 g, 4.19 mmol, 52%).

Aufarbeitung

  1. temperatureThen, the solution was heated
  2. temperatureto reflux for 24 h
  3. temperatureThe solution was cooled to 25° C.
  4. concentrationconcentrated
  5. additionpoured into saturated aqueous NaHCO3 (50 mL)
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9300128f3e0144c191cb7471cf6d67b0
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169798B2

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