Extracurricular laboratory: Synthetic route of 6-Bromo-2,3′-bipyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference of 106047-28-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem