Synthetic Route of 1033610-45-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1033610-45-5, name is 4-Bromo-3,5-dimethoxypyridine. A new synthetic method of this compound is introduced below.
To an ice-cooled suspension of sodium hydride (60% dispersion in mineral oil, 650 mg, 16.3 mmol) in dry DMF (10 ml) was added 4-methoxybenzyl alcohol (2.24 g, 16.3 mmol) drop-wise via syringe. Vigorous evolution of hydrogen was observed and the reaction was allowed to warm to room temperature and stirred for 15 minutes. 4-Bromo-3,5-dimethoxypyridine (1.17 g, 5.41 mmol) was added and the reaction heated to 900C overnight. After cooling, only trace starting material could be detected by TLC analysis and the reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water 3 times then brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted sequentially with EtOAc : hexanes, 2:1, 1:0) to give the product as a tan solid (865 mg, 58%). 1H-NMR (300 MHz, CDCl3) delta 7.96 (s, 2H), 7.33 (d, J= 8.5 Hz, 2H), 6.84 (d, J= 8.5 Hz, 2H), 5.11 (s, 2H), 3.89 (s, 6H), 3.78 (s, 3H). MS (ES+) m/z 276.1 (M + H+).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033610-45-5, 4-Bromo-3,5-dimethoxypyridine, and friends who are interested can also refer to it.
Reference:
Patent; BIONOMICS LIMITED; WO2008/70908; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem