Extracurricular laboratory: Synthetic route of 6-Bromo-1H-pyrazolo[4,3-b]pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.Formula: C6H4BrN3

6-bromo-1H-pyrazolo[4,3-b]pyridine (400 mg, 2.0 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.4 mmol), K2CO3 (828 mg, 6 mmol), and Pd(dppf)Cl2(81.7 mg, 0.1 mmol) were dissolved in the solvent of 1,4-dioxane/H2O (v/v = 3:1, 20 mL). The resultingmixture was stirred at 80 C under Ar for 2 h. Then, the reaction mixture was evaporated to dryness.The residue was purified by flash chromatography to give compound 39 as a yellow hairy solidwith the yield of 82%. 1H-NMR (300 MHz, DMSO-d6, ppm) 13.29 (s, 1H), 8.80 (s, 1H), 8.36 (s, 1H),8.24 (s, 1H), 8.07 (s, 2H), 3.90 (s, 3H). ESI-MS: C10H10N7O2S, Exact Mass: 199.09, m/z 200.0 (M + 1)+.Retention time 2.51 min, >95% purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Alan; Liu, Qiufeng; Wang, Ruifeng; Wei, Peng; Dai, Yang; Wang, Xin; Xu, Yechun; Ma, Yuchi; Ai, Jing; Shen, Jingkang; Ding, Jian; Xiong, Bing; Molecules; vol. 23; 3; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem