Preparation and application of 2,6-dichloro-3-hydroxypyridine_Industrial additives

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