Uses
2,6-Dibromo-3-aminopyridine is an important novel heterocyclic organic intermediate, and currently there are no truly industrial-scale production facilities in China. Furthermore, it is an important industrial raw material, widely used in the pharmaceutical, pesticide, and dye industries.
Chemical Properties
Brown powder
Definition
2,6-Dibromopyridin-3-amine is a deviate of 2, 6-dibromo pyridine,, a traditional organic chemistry product. 2, 6-dibromo pyridine is water insoluble, can be dissolved in methyl alcohol, ethanol, dioxane, chloroform, etc., be mainly used in the high-end Field of Fine Chemicals such as medicine, agricultural chemicals, can generate 2,6-dioctyl phthalate ethyl ester pyridine, be used for the exploitation of engineering plastics and novel pesticide and pharmaceutical prod.
Synthesis
General procedure for the synthesis of 2,6-dibromo-3-aminopyridine from 3-aminopyridine:
Method F; Example F-1; 4-({6-bromo-2-oxo-1-[2-(trifluoromethyl)benzyl]-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-3-ylmethyl})benzoic acid; F-1-a Preparation of 2,6-dibromo-3-pyridinamine.
Reference to Majumdar, K.C.; Mondal, S. (Regioselective synthesis of substituted pyrrolidinopyridines based on Pd(II)-mediated cross-coupling and base-induced heterocyclization. Springer. 2007, 48, 6951-6953), 3-aminopyridine (4.75 g, 50.5 mmol) was dissolved in a mixture of DMSO (100 mL) and water (2.5 mL) at 0 °C, and N-bromosuccinimide (18.9 g, 8.91 mmol) was added in batches. The reaction mixture was stirred at room temperature for 24 hours. The solid formed during the reaction was collected by filtration and dried over a glass stock. Subsequently, the dried solid was dissolved in ethyl acetate, dried with sodium sulfate and filtered. The solvent was removed by vacuum evaporation to give a reddish brown solid product (11.7 g, 92%). The product was used directly in the subsequent reaction without further purification and its 1H NMR spectrum was in agreement with literature reports (Parlow, J.J.; Kurumbail, R.G.; Stegeman, R.A.; Stevens, A.M.; Stallings, W.C.; South, M.S. Design, Synthesis and Crystal Structure of Selective 2-Pyridone Tissue Factor VIIa Inhibitors. (J. Med. Chem. 2003, 46, 4696-4701) conform.
References
[1] Tetrahedron Letters, 2007, vol. 48, # 39, p. 6951 - 6953
[2] Synthesis, 2001, # 14, p. 2175 - 2179
[3] Patent: WO2010/116270, 2010, A1. Location in patent: Page/Page column 50-51
[4] Patent: KR2015/52989, 2015, A. Location in patent: Paragraph 0357-0362
[5] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 14083 - 14093
