Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative
19 February 2003 (online)
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
SilvermanRB. The Organic Chemistry of Drug Design and Drug Action Academic Press; San Diego: 1992.
IskricS. Period. Biol. 1984, 86: 153
KulmaczRJ. J. Biol. Chem. 1989, 264: 14136
ConnorHE. BeattieDT. Migraine: Pharmacology and Genetics SandlerM. FerraryM. HarnettS. Chapman and Hall; London: 1996. p.30
WielandT. FischerE. MoewusF. Liebigs Ann. Chem. 1949, 561: 47
CokerN. J. Org. Chem. 1962, 27: 1881
ThompsonME. J. Org. Chem. 1984, 49: 1700