Ethyl bromopyruvate → Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

HRID 1174118

Reaktionsgleichung

Reaktionsgleichung von HRID 1174118
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[S:9])[NH2:8].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:9][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]=1

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 1549499Pyridine-2-carbothioamide

Produkt 1

HCID 10082761Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylateAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of the product of Example 3H (25.4 mmol) in ethanol (50 mL) was treated with ethyl bromopyruvate (3 mL, 23.9 mmol) and molecular sieves (10 g, 3 Å), heated at reflux for 16 hours, cooled to 25° C., filtered and concentrated. The concentrate was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane to give the title compound (1.98 g, 33% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and saturated NaHCO3
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7a125277526f45339d6f7ae805fcaa7b
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834043B2

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