Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate

110543-98-1

108-98-5

131707-24-9

To 900 mL of methanol was added 30 g of sodium hydroxide (0.75 mol) and stirred until completely dissolved to form a clarified solution. Subsequently, 39.7 g of benzenethiol (0.36 mol) was added to this solution and the reaction was continued with stirring for 2 hours. Next, 130 g of ethyl 1-methyl-2-(bromomethyl)-5-acetoxy-6-bromoindole-3-carboxylate (0.30 mol) was added and the reaction was continued with stirring for 3 hours. Upon completion of the reaction, the reaction mixture was neutralized with acetic acid and a large amount of solid was observed to precipitate. The mixture was allowed to stand, the solid was collected by filtration and the filter cake was washed with cold water. Finally, the crude product was recrystallized from ethyl acetate and dried to give 114.5 g of ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylthiomethyl)indole-3-carboxylate in 90.8% yield.