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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).
Hazard Statements: H302-H315-H319-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant