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Synthesis 2003(3): 0383-0388
DOI: 10.1055/s-2003-37354
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative

Alexander M. Korolev, Andrey E. Shchekotikhin, Ludmila N. Lysenkova, Maria N. Preobrazhenskaya*
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, B. Pirogovskaya 11, Moscow 119021, Russia
Fax: +7(095)2450295; e-Mail: lcta@space.ru;
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Publication History

Received 5 November 2002
Publication Date:
19 February 2003 (online)

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Abstract

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.

Key words

(indol-3-yl)methanesulfonamide - sodium (indol-3-yl)methanesulfonate - indoxyl - (N-tert-butyl)methanesulfonamide - (5-methoxyindol-3-yl)methanesulfonamide