Bromoethene → 2-Methyl-5-(1,2-oxazol-3-yl)pyridine

HRID 271468

Reaktionsgleichung

Reaktionsgleichung von HRID 271468
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][CH:5]=1.[CH:12](Br)=[CH2:13].CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[CH3:10][C:7]1[N:6]=[CH:5][C:4]([C:3]2[CH:13]=[CH:12][O:1][N:2]=2)=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11641BromoetheneHCID 16682746Bis(tributyltin) oxideHCID 72574142N-hydroxy-6-methylnicotinimidoyl chloride

Produkt 1

HCID 598348122-Methyl-5-(1,2-oxazol-3-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To crude N-hydroxy-6-methylnicotinimidoyl chloride in 10 mL toluene was added vinyl bromide (1 M in THF, 11 mL, 11.0 mmol), followed by bis(tributyltin)oxide (2.12 g, 1.87 mL, 3.67 mmol). The reaction mixture was stirred at room temperature for 5 h and then concentrated. The crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 155 mg (26%, for two steps) of the title compound as a white solid. HPLC/MS: retention time=0.39 min, [M+H]+=161.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a527b3f7fb7940faaeb308a3ce3d3f1a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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