Preparation and application background and overview of 2,6-dichloro-3-hydroxypyridine
2,6-Dichloro-3-hydroxypyridine is a pharmaceutical intermediate that can be obtained by the reaction of 2,6-dichloropyridin-3-ylboronic acid and hydrogen peroxide. There are reports in the literature that it can be used to prepare drugs against HCV infection.
Preparation and application of 2,6-dichloro-3-hydroxypyridine
Chloropyridine
At 0°C, H2O2 (1.60 g, 47.12 mmol) was slowly added to compound 2,6-dichloropyridin-3-yl Boric acid (3 g, 15.71 mm methoxypyridine ol) in CH2Cl2 (30 ml). After stirring at room temperature for approximately 15 hours, the mixture was quenched with saturated aqueous Na2S2O3 (50 mL) and treated with 1N Adjust to pH<7 with HCl. The mixture was extracted with EtOAc (40 ml x 3). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered, and the solvent was concentrated in vacuo to provide 2,6-dichloro-3-hydroxypyridine ( 2.34 g, yield: 91.4%). 1H-NMR(CDCl3, MHz)δ 7.30(d, J=8.4 Hz, 1H), 7.19(d, J=8.4 Hz, 1H), 5.70 (br, 1H). MS(M+H)+: 164/166/168.
Preparation and application of 2,6-dichloro-3-hydroxypyridine
2,6-Dichloro-3-hydroxypyridine can be used to prepare compounds with the following tetracyclic heterocyclic structure 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethyl Sulfonylamino)-5-(6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)benzofuran-3 -Carboxamide, this compound can be used to treat or prevent HCV infection in patients. Hepatitis C virus (HCV) infection is a serious health problem causing chronic liver diseases, such as cirrhosis and hepatocellular carcinoma, in a significant number of infected individuals. Current treatments for HCV infection include immunotherapy with recombinant interferon-α alone or in combination with the nucleoside analog ribavirin. There is a clear and long-felt need for effective therapies to treat HCV infection. Specifically, there is a need to develop compounds that selectively inhibit HCV viral replication and be used to treat HCV-infected patients.
References
[1] [Invented in China] CN201280050985.8 Tetracyclic heterocyclic compounds and their use in treating viral diseases
