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Dimethyl Disulfide → ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

HRID 12617
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12617
CS[S:3][CH3:4].S(Cl)(Cl)(=O)=O.[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:17]([S:3][CH3:4])=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 66738782ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate

Produkt 1

HCID 68693460ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a chloroform (0.8 mL) solution of dimethyl disulfide (30 mg), sulfuryl chloride (34 mg) was added at −15° C. and the mixture was stirred at −5° C. for 1.5 hours. To the reaction mixture, a chloroform (0.5 mL) solution of the compound prepared in Example 43, namely, ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate (100 mg) was added at −78° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9) to obtain the titled compound having the following physical properties (70 mg).

Aufarbeitung

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9)

Quellen und Nachweise

ORD-Eintrag
ord-89b9fac623f644f58e5b221f3871bc84
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728023B2

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