Methyl iodide → methyl 4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylate

Participants

Reaction Steps

To a mixture of Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate (0.6 g) in THF (10 mL) was added potassium carbonate (0.309 g) and iodomethane (0.63 mL). The mixture was stirred at room temperature for 4 h then heated to 40° C. overnight. Iodomethane (0.3 mL) was added and the mixture heated an additional 3 h. The mixture was cooled to room temperature, partitioned between water and diethyl ether, dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in ether and decolorizing carbon (2 g) was added and the mixture refluxed for 5 minutes then filtered through celite while hot. The ether was removed under reduced pressure to give 0.437 g of the title compound: MS (ESI+) for C12H14 N2 O4 SI m/z 321.1 (M+K).

Provenance & Evidence