Synthetic Route of 1256805-54-5, 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.
To a solution of 6-chloro-4-methoxypyridin-3-ylamine (0.95 mmol, 160 mg) in dichloromethane (1 mL) and pyridine (2 mmol, 165 microliter) (3,4-dichlorophenyl)- methanesulfonyl chloride ((275 mg, 0.95 mmol) was added and the mixture was stirred overnight and then concentrated on a rotary evaporator. To the residue ethanol (99.5 %, 5 mL) and NaOH (1 M, 2 mL) were added and the mixture was heated at 60 C until all material went into solution (took less than 5 min). The mixture was cooled, water (5 mL) and glacial acetic acid were added to pH 3-4 (checked with pH sticks). The precipitate was collected by filtration and dried to afford the intermediate N-(6-chloro-4-methoxy- pyridin-3-yl)-3,4-dichlorophenyl-methanesulfon-amide which was dissolved in dichloromethane (2 mL), cooled on an ice-bath and boron tribromide (1M solution in dichloromethane, 2 mmol, 2 mL) was added dropwise. The mixture was stirred at room temperature overnight. The mixture was then partitioned between dichloromethane and aqueous sodium hydroxide at pH 13. The aqueous phase was collected, pH was adjusted to approx. 3-4 with acetic acid and the mixture was extracted with ethylacetate (20 mL). The organic phase was collected and evaporated and the residue was crystallized from methanol/water to afford the title compound (158 mg, 43%).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, and friends who are interested can also refer to it.
Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem