Acetic Acid → Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

Participants

Reaction Steps

To a solution of methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (33.2 g; 135 mmol), prepared as in Example 1, step 4, in 300 mL toluene and 150 mL acetic acid was added sodium acetate (12.7 g; 155 mmol) followed by 1-(4-chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine (48.4 g; 143 mmol), prepared as in step 4. The reaction mixture was stirred in the dark for 5 days, then was poured into water and extracted with ethyl acetate. Solid sodium bicarbonate was added to the extracts and then filtered. The filtrate was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The product was isolated by flash chromatography (40% diethyl ether in hexane) and then recystallized from ethyl acetate/hexane to yield methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate.

Provenance & Evidence