Use | 4-chloro-1h-pyrrolo [2,3-B] pyridine-5-carbonitrile can be used in the field of biological research. The pyrrolo pyridine skeleton can be divided into pyrrolo [3,2-b] pyridine, pyrrolo [3,4-b] pyridine, pyrrolo [2,3-b] pyridine and other six different structures. Pyrrole and pyridine compounds are cyclized to form heterocyclic compounds with pyrrolopyridine or structural characteristics, which show potential biological activities, many new active intermediates then become important raw materials in the synthesis of drugs, design and innovative synthesis of excellent biological activity, less toxic side effects of drugs, research topics that are always of common concern and great interest to developers of organic synthesis and pharmaceutical research. Such derivatives are present in alkaloids such as ASP3627, mappicin, Vemurafenib and the like, and can be used as LRRK2 inhibitors, MPS1 inhibitors, JAK1 inhibitors, Met kinase inhibitors and the like. |
preparation of | framework pyrrolo [2,3-B] pyridine the bicyclic parent structure has been reported in many ways, pyridine 3-dicarboxylate as raw material, by esterification, reduction, chlorination, then with sodium hydride and p-toluenesulfonamide for cyclization, preparation of pyrrolo pyridine ring compounds, intramolecular cyclization may also occur to prepare 4-chloro-1h-pyrrolo [2,3-B] pyridine-5-carbonitrile, and the synthesis reaction scheme is shown below. Fig.1 reaction scheme for the synthesis of 4-chloro-1h-pyrrolo [2,3-B] pyridine-5-carbonitrile: 3-ethyne-4-chloropyridine-2-amine-5-carbonitrile was dissolved in anhydrous methanol, and a catalytic amount of glacial acetic acid was added, and weigh 70.0 mg (1.10 mmol) sodium cyanoborohydride in N 2 gas, mix well in the flask, stir and heat to 60 ℃, track and detect the reaction progress by thin layer chromatography, and stop the reaction until no reactant is found, TLC detection (methanol developing solvent), product Rf = 0.57. The reaction mixture was dissolved in dichloromethane and washed twice with water. The organic phase was dried over anhydrous sodium sulfate and the mixture was separated by silica gel column chromatography, the product was dried in vacuo to give 4-chloro-1h-pyrrolo [2,3-B] pyridine-5-carbonitrile. |