Cesium carbonate → Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 486093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486093
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.Cl.Cl[CH2:34][C:35]1[N:36]=[C:37]([CH3:40])[S:38][CH:39]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:34][C:35]4[N:36]=[C:37]([CH3:40])[S:38][CH:39]=4)=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 14980577Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Produkt 1

HCID 19097505Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (Preparation 2) (25 g), 4-chloromethyl-2-methylthiazole hydrochloride (Maybridge Chemical Co., Ltd.) (11.6 g) and Cs2CO3 (68.7 g) in 250 mL of CH3CN were heated at reflux for 24 hours. The mixture was cooled, poured onto water, and extracted (2× EtOAc), washed twice with brine, dried (MgSo4), and evaporated. Chromatography of the residue on silica gel eluting with hexane/EtOAc 4:1 afforded the title compound as a solid.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. additionpoured onto water
  4. extractionextracted (2× EtOAc)
  5. washwashed twice with brine
  6. customdried (MgSo4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0f741723648b47b78d6eebd137cf3032
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290798

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