Potassium Carbonate → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester

HRID 925277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925277
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[SH:12])=[O:5])[CH3:2].Br[CH2:14][CH2:15][C:16]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([F:18])[F:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[S:12][CH2:14][CH2:15][C:16]([F:18])([F:17])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15077130Ethyl 2-methyl-4-sulfanyl-1,3-thiazole-5-carboxylateHCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

Produkt 1

HCID 867201714-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of give 4-mercapto-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.58 g, 2.83 mmol) in acetone (10 ml) are added 1-(3-bromo-1,1-difluoro-propyl)-4-fluoro-benzene (synthesized according to the methods described in sections a) to e) of example 1) (0.72 g, 2.83 mmol) and potassium carbonate (0.78 g, 5.66 mmol) an the mixture is heated at 80° C. for 16 h. Acetone is evaporated, diluted with water (40 ml) and extracted with EtOAc (3×30 ml). The crude product is purified by column chromatography (silica gel, 10% EtOAc/hexane) yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.6 g, 1.6 mmol, 56%).

Aufarbeitung

  1. customsynthesized
  2. customAcetone is evaporated
  3. additiondiluted with water (40 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. customThe crude product is purified by column chromatography (silica gel, 10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-70b467d4f7d1439c82e361e80e93ca53
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284286B2

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