106331-71-9

Basic information

• Product Name: 2,3-dibromo-5,6-dimethoxypyridine
• Synonyms: 2,3-dibromo-5,6-dimethoxypyridine
• CAS NO: 106331-71-9
• Molecular Formula: C₇H₇Br₂NO₂
• Molecular Weight: 296.94398
• Mol File: 106331-71-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-dibromo-5,6-dimethoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dibromo-5,6-dimethoxypyridine(106331-71-9)
• EPA Substance Registry System: 2,3-dibromo-5,6-dimethoxypyridine(106331-71-9)

Safety Data

• Hazardous Substances Data: 106331-71-9(Hazardous Substances Data)

Usage

General Description

2,3-dibromo-5,6-dimethoxypyridine is a chemical compound with the molecular formula C7H6Br2N2O2. It is a pyridine derivative with two bromine atoms and two methoxy groups attached to the aromatic ring. 2,3-dibromo-5,6-dimethoxypyridine is used in organic synthesis as a reagent for various reactions, including Suzuki-Miyaura cross-coupling and Sonogashira coupling reactions. It is also used in the pharmaceutical industry as an intermediate in the synthesis of potential drug candidates. 2,3-dibromo-5,6-dimethoxypyridine is a versatile building block for the preparation of complex organic molecules and has applications in medicinal chemistry and material science.

Upstream product

• 52605-97-7 2,3-dimethoxypyridine 
• 6636-78-8 2-chloro-3-hydroxypyridine 
• 52605-96-6 2-chloro-3-methoxypyridine 

Downstream Products

• 106331-72-0 5-bromo-2,3,6-trimethoxypyridine 
• 1333147-23-1 2-(biphenyl-3-yl)-3-bromo-5,6-dimethoxypyridine 
• 1333147-28-6 3-(biphenyl-3-yl)-2-bromo-5,6-dimethoxypyridine 
• 1333147-33-3 2-(biphenyl-3-yl)-5,6-dimethoxypyridine-3-carbonitrile 
• 1333146-70-5 2-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-3-carbonitrile 
• 1333147-39-9 3-(biphenyl-3-yl)-5,6-dimethoxypyridine-2-carbonitrile 
• 1333146-72-7 3-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-2-carbonitrile 
• 1581767-04-5 6-bromo-5-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one 
• 1581767-03-4 5-bromo-6-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one 
• 1469896-46-5 5-bromo-6-(4-fluorophenyl)-2,3-dimethoxypyridine 
• 1469896-44-3 6-bromo-5-(4-fluorophenyl)-2,3-dimethoxypyridine 
• 1581767-40-9 2,3-dimethoxy-5,6-bis(3-fluorophenyl)pyridine 
• 1581767-05-6 6-bromo-5-(3-fluorophenyl)-3-hydroxypyridin-2(1H)-one 
• 1581767-06-7 5-bromo-6-(3-fluorophenyl)-3-hydroxypyridin-2(1H)-one 

Relevant articles and documents

Aryl and Arylalkyl Substituted 3-Hydroxypyridin-2(1H)-ones: Synthesis and Evaluation as Inhibitors of Influenza A Endonuclease

Seasonal influenza infections are associated with an estimated 250–500 000 deaths annually. Resistance to the antiviral M2 ion-channel inhibitors has largely invalidated their clinical utility. Resistance to neuraminidase inhibitors has also been observed in several influenza A virus (IAV) strains. These data have prompted research on inhibitors that target the cap-snatching endonuclease activity of the polymerase acidic protein (PA). Baloxavir marboxil (Xofluza), recently approved for clinical use, inhibits cap-snatching endonuclease. Resistance to Xofluza has been reported in both in vitro systems and in the clinic. An X-ray crystallographic screening campaign of a fragment library targeting IAV endonuclease identified 5-chloro-3-hydroxypyridin-2(1H)-one as a bimetal chelating agent at the active site. We have reported the structure–activity relationships for 3-hydroxypyridin-2(1H)-ones and 3-hydroxyquinolin-2(1H)-ones as endonuclease inhibitors. These studies identified two distinct binding modes associated with inhibition of this enzyme that are influenced by the presence of substituents at the 5- and 6-positions of 3-hydroxypyridin-2(1H)-ones. Herein we report the structure–activity relationships associated with various para-substituted 5-phenyl derivatives of 6-(p-fluorophenyl)-3-hydroxypyridin-2(1H)-ones and the effect of using naphthyl, benzyl, and naphthylmethyl groups as alternatives to the p-fluorophenyl substituent on their activity as endonuclease inhibitors.

Synthetic method of 2,5,6-trimethoxy-3-picolinic acid

The invention relates to a synthetic method of 2,5,6-trimethoxy-3-picolinic acid, which mainly solves the technical problem that no effective synthetic methods are provided at present. The synthetic method provided by the invention comprises the following steps: converting 2-chloro-3-hydroxypyridine hydroxy into methoxy; carrying out methoxy nucleophilic substitution of chlorine; carrying out bromination of a pyridine ring; and carrying out methoxy selective substitution of bromine; removing bromine from n-butyllithium, reacting with carbon dioxide, and introducing carboxy so as to obtain 2,5,6-trimethoxy-3-picolinic acid. In the whole synthetic process, intermediates and object products do not need to be separated through a chromatographic column, the raw materials are cheap, and the purification is simple.

THERAPEUTIC HYDROXYPYRIDINONES, HYDROXYPYRIMIDINONES AND HYDROXYPYRIDAZINONES

The invention provides compounds of formula (I): and salts and prodrugs thereof wherein R4, X1 and X2 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.