Diethyl Ether → 5-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methoxy)-1H-indole

HRID 2215105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215105
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl[CH2:12][C:13]1[S:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:15][C:14]=1[CH3:28].[Cl-].C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>C(#N)C.O>[CH3:28][C:14]1[N:15]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[S:17][C:13]=1[CH2:12][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 21949469Chloride 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Produkt 1

HCID 219494915-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methoxy)-1H-indoleAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-Hydroxyindole (200 mg, 1.5 mmol) was dissolved in acetonitrile (10 mL) with the chloride 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.50 g, 1.7 mmol) and Cs2CO3 (2.37 g, 7.27 mmol) The reaction mixture was stirred at RT overnight. Ether (50 mL) and H2O were added and stirring was continued for another 5 min. The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined organics was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluted with EtOAc and hexanes to give the desired product as a white solid (0.3 g, 51% yield).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for another 5 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (2×100 mL)
  5. dry with materialThe combined organics was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluted with EtOAc and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c143c58c3a45444fbd1ef2a04935d8fa
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109222B2

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