Category: 17368-12-6

17368-12-6 , The common heterocyclic compound, 17368-12-6, name is 2-Chloro-4-hydroxypyridine, molecular formula is C5H4ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Method N. tert-Butyl 2-((2-acetylpyridin-4-yl)oxy)acetate To a solution of 2-chloropyridin-4-ol (500mg, 3.9mmol, l eq) in DMF (10ml) at 0C, was added NaH (60%, 188mg, 4.7mmol, 1.2 eq). After stirring 10 min at 0C, tert-butyl 2- bromoacetate (694ul, 4.7 mmol, 1.2 eq) was added, and the reaction was stirred an additional 20 minutes. The reaction was quenched with saturated aqueous ammonium chloride and partitioned in EtOAc/water. The organic was washed 2 x water, 1 x brine, dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography to yield tert-butyl 2-((2-chloropyridin-4-yl)oxy)acetate (793 mg, 83% yield) as a clear oil. 2-chloropyridin-4-ol (lOOmg, 0.41mmol, l eq), tributyl(l-ethoxyvinyl)stannane (166ul, 0.49mmol, 1 .2eq), PdCl2(PPh3)2 (14mg, 0.021mmol, 0.05 eq), in DMF (1 ml) was degassed under bubbling nitrogen and heated in a microwave reactor for 10 minutes at 140C. The reaction was partitioned in EtO Ac/water, extracted 3 x EtOAc, washed 3 x water, 1 x brine, dried over sodium sulfate and concentrated. The product was purified by silica gel chromatography to afford tert-butyl 2-((2-( l -methoxyvinyl)pyridin-4-yl)oxy)acetate (65 mg, 57% yield) as a light orange oil. tert-butyl 2-((2-(l-methoxyvinyl)pyridin-4-yl)oxy)acetate (230mg, 0.824 mmol, 1 eq) was dissolved in DCM (10ml). To this solution was added HCl/ether (2M, 2 ml). The reaction was stirred 3 hours at RT and concentrated under reduced pressure. rt-Butyl 2- ((2-acetylpyridin-4-yl)oxy)acetate (110 mg, 53% yield) was isolated as a white solid after purification by silica gel chromatography.

According to the analysis of related databases, 17368-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; AUGERI, David, J.; BENCIVENGA, Anthony, F.; BLANDEN, Adam; CARPIZO, Darren, R.; GILLERAN, John, A.; KIMBALL, Spencer David; LOH, Stewart, N.; YU, Xin; (70 pag.)WO2016/123253; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

17368-12-6, 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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine. A new synthetic method of this compound is introduced below.

A mixture of 5-fluoro-4-methyl-2-nitropyridine (2 g, 12.81 mmol) and 2-chloro-4-hydroxypyridine (1.66 g, 12.81 mmol) in DMF (26 mL) was sparged with Ar, treated with K2CO3 (2.66 g, 19.22 mmol), heated at 88 C. for 24 h, then at 50 C. for 2 days. The mixture was treated with water and the resulting solid collected via filtration and dried to afford 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (2.72 g, 80%). 1H NMR (400 MHz, DMSO-d6): delta 8.49 (s, 1H), 8.47 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 7.24 (d, J=2.3 Hz, 1H), 7.12 (dd, J=5.7, 2.3 Hz, 1H), 2.32 (s, 3H); MS (ESI) m/z: 266.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem