Dimethyl Disulfide → Methyl 4,7-dimethyl-3-methylsulfenylindole-2-carboxylate

Participants

Reaction Steps

Under ice-cooling, 0.89 ml (7.4 mmol) of dimethyl disulfide was dissolved in 20 ml of 1,2-dichloroethane, and 0.53 ml (6.5 mmol) of sulfuryl chloride was added. The reaction mixture was stirred for 20 minutes and a solution of 2.00 g (9.8 imnol) of methyl 4,7-dimethylindole-2-carboxylate in 10 ml of anhydrous DMF was added. The reaction mixture was stirred for 2 hours, then dissolved in ethyl acetate and washed with water. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide 1.94 g of white crystals. Yield: 80%

Provenance & Evidence