Réaction #40895

Équation de réaction

ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate

dimethyl disulfide

sulfuryl chloride

sodium hydrogen carbonate

→

titled compound

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

Solvants

chloroform

chloroform

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source