5-Fluoro-2-methylindole

5-Fluoro-2-methylindole is a chemical intermediate that can be used in the synthesis of other compounds. It is a versatile building block with many applications, such as being a useful intermediate for the synthesis of heterocyclic compounds. This compound reacts with aniline to form 2,6-diaminopyridine, which has been shown to have anti-inflammatory properties.

5-fluoro-2-methylindole was prepared via the Fischer indole synthesis and served as a key indole starting material for constructing a series of aminoalkylindole (AAI) derivatives[3].

5-Fluoro-2-methylindole (5-Fluoro-2-methyl-1H-indole) is a 5-substituted-2-methyl-1H-indole.

1-(5-fluoro-2-nitrophenyl) propane-2-one (0.5mmol, 99 mg), zinc powder (3.0mmol, 196 mg), and acetic acid (6.0mmol, 360 mg) was added to the reaction tube, followed by adding ethanol to 2 ml at 90 °C for 3h. After cooling to room temperature, the reaction system was added 20 ml water. 5-Fluoro-2-methylindole was obtained after purification. 

Very soluble in N,N-Dimethylformamide,Soluble in methanol,Sparingly soluble inglacial acetic acid, Very slightly soluble inchloroform, Practically insoluble in water.

[1] Organic and Biomolecular Chemistry,  2016,  vol. 14,  # 44,  p. 10511 - 10515
[2] Patent: CN106631968,  2017,  A. Location in patent: Paragraph 0069-0072; 0074
[3] Eissenstat, M. A., Bell, M. R., D'Ambra, T. E., Alexander, E. J., Daum, S. J., Ackerman, J. H., Gruett, M. D., Kumar, V., Estep, K. G. (1995). Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics. Journal of Medicinal Chemistry, 38(16), 3094–3105. https://doi.org/10.1021/jm00016a013