I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.
Ran Jiang.; Hai-Yan Xu.; Xiao-Ping Xu.; Xue-Qiang Chu.; Shun-Jun Ji. Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues. Organic & Biomolecular Chemistry. 2011, 9, (16), 5659-5669.
Eduard Dolusic.; Pierre Larrieu.; Laurence Moineaux.; Vincent Stroobant.; Luc Pilotte.; Didier Colau.; Lionel Pochet.; Benoît Van den Eynde.; Bernard Masereel.; Johan Wouters.; Raphaël Frédérick. Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Journal of medicinal and pharmaceutical chemistry. 2011, 54 (15), 5320-5334.
Can be dimetallated using the n-BuLi/KO-t-Bu system. Reaction with electrophiles (methyl iodide, benzophenone, t-butyl isocyanate) then occurs preferentially at the more reactive methyl position: J. Chem. Soc., Perkin 1, 179 (1990).
An alternative approach to functionalization of the 2-methyl group involves low-temperature N-lithiation followed by reaction with dimethyl carbonate to give the 1-methoxycarbonyl derivative. NBS ɑ-bromination then allows nucleophilic substitution to give a variety of 2-substituted indoles: Synthesis, 743 (1992).
Undergoes a mild, selective C-3 reductive alkylation in the presence of Triethylsilane, A10320, and TFA; e.g. with benzaldehyde, the 3-benzyl derivative is formed in 88% yield: Tetrahedron Lett., 34, 1529 (1993).
해저드 설명서 (EU): H318
Causes serious eye damage.
주의 설명서: P280i-P305+P351+P338-P310a
Wear eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor