Potassium Carbonate → Ethyl 3-[1-(p-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-3-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

Participants

Reaction Steps

A suspension of ethyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropionate (3.0 g; 6.5 mmol), prepared as in step 4, 3-picolyl chloride hydrochloride (1.1 g; 6.5 mmol), and powdered potassium carbonate (2.7 g; 19.5 mmol) in 20 mL dimethylformamide (DMF) was stirred at ambient temperature for 4 days. The reaction mixture was diluted with brine and extracted with ethyl acetate. The extracts were dried over magnesium sulfate and concentrated. The resulting residue was subjected to flash chromatography on silica gel (70% diethyl ether in hexane) to give ethyl 3-[1-(p-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-3-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate as a pale yellow oil containing a small amount of DMF.

Provenance & Evidence