Two methods for the synthesis of (indol-3-yl)methanesulfonamide
were elaborated based on the ‘switching off’ the
reactivity of the indole nucleus in the intermediates by using indoline
or indoxyl compounds. (2,3-Dihydroindol-3-yl)methanesulfonic acid was
the key compound used in the indole-indoline approach and (1-acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-(tert-butyl)methanesulfonamide
was the key intermediate when 1-acetylindoxyl was used as the starting
compound.
(indol-3-yl)methanesulfonamide - sodium (indol-3-yl)methanesulfonate - indoxyl - (N-tert-butyl)methanesulfonamide - (5-methoxyindol-3-yl)methanesulfonamide
