Cesium carbonate → 4-(2-Amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl ester

HRID 1889176

Reaktionsgleichung

Reaktionsgleichung von HRID 1889176
Br.Br[C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1.[CH2:9]([O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:9]([O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:3]2[S:7][C:6]([NH2:8])=[N:5][CH:4]=2)=[C:15]([F:20])[CH:14]=1)[CH3:10]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

Produkt 1

HCID 596100274-(2-Amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl esterAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 5-Bromothiazole-2-amine hydrobromide (1.55 g, 5.97 mmol) in acetone (100 mL) was added 3-fluoro-4-hydroxy benzoic acid ethyl ester (1.1 g, 5.97 mmol) and cesium carbonate (3.89 g, 11.94 mmol) under argon atmosphere and refluxed for 5 hrs. The reaction mixture was cooled to room temperature and filtered; the filtrate was concentrated under reduced pressure. The residue was partitioned in between ethyl acetate and water. The layers were separated, the organic layer was washed with cold 2 N NaOH (10 mL), brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 4-(2-amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl ester (0.68 gm).

Aufarbeitung

  1. temperaturerefluxed for 5 hrs
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned in between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed with cold 2 N NaOH (10 mL), brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60ba5f9922b243679e09b2979a23c471
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501955B2

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