16273-54-4

Basic information

• Product Name: 5-bromo-2-methoxypyridine
• Synonyms: 3-(N-Methylformimidoyl)pyridine;alpha-(Methylimino)-3-picoline;N-Methyl-N-(3-pyridylmethylene)amine;MethanaMine, N-(3-pyridinylMethylene)-;N-(Pyridin-3-ylMethylene)MethanaMine;methyl-pyridin-3-ylmethylene-amine;N-(3-pyridinylmethylene)Methanamine
• CAS NO: 16273-54-4
• Molecular Formula: C₇H₈N₂
• Molecular Weight: 120.154
• Mol File: 16273-54-4.mol

Chemical Properties

• Boiling Point: 212℃
• Flash Point: 82℃
• Appearance: /
• Density: 0.96
• Vapor Pressure: 0.254mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 2-8°C
• PKA: 3.95±0.12(Predicted)
• CAS DataBase Reference: 5-bromo-2-methoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-methoxypyridine(16273-54-4)
• EPA Substance Registry System: 5-bromo-2-methoxypyridine(16273-54-4)

Safety Data

• Hazardous Substances Data: 16273-54-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-bromo-2-methoxypyridine is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structural features allow it to be a key component in the creation of novel drugs with potential applications in various therapeutic areas.
Used in Chemical Research:
In the field of chemical research, 5-bromo-2-methoxypyridine serves as a valuable building block for the synthesis of complex organic molecules. Its reactivity and functional groups make it an attractive candidate for further chemical modifications and the development of new materials with specific properties.
Used in the Synthesis of Organophosphorus Compounds:
5-bromo-2-methoxypyridine is used as a reagent in the preparation of new organophosphorus-substituted fulvenes with indenyl moieties, as demonstrated by the example of (E)-N-(Pyridin-3-ylmethylene)methanamine. This application highlights its utility in the synthesis of complex and potentially valuable organic compounds with diverse applications.

InChI:InChI=1/C7H8N2/c1-8-5-7-3-2-4-9-6-7/h2-6H,1H3/b8-5+

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 74-89-5 methylamine 

Downstream Products

• 119383-02-7 (-)-trans-3,5-dimethyl-2-(pyridin-3-yl)-thiazolidin-4-one 
• 119383-00-5 (2R,5S)-(+)-cis-3,5-Dimethyl-2-(3-pyridyl)thiazolidin-4-one 
• 119383-00-5 (+/-)-cis-3,5-Dimethyl-2-(3-pyridyl)thiazolidin-4-one 
• 119383-00-5 (+/-)-trans-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one 
• 114898-14-5 (+/-)-cis-3-methyl-5-phenyl-2-(3-pyridyl)thiazolidin-4-one 
• 114898-14-5 (+/-)-trans-3-methyl-5-phenyl-2-(3-pyridyl)thiazolidin-4-one 
• 116947-40-1 1-methylthio-3-(3-pyridyl)-1,2-cyclopropanedicarboxylic acid diethyl ester 
• 124-40-3 dimethyl amine 
• 114898-02-1 (+/-)-cis-5-(4-Chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 
• 114898-02-1 (+/-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 
• 124623-49-0 (2R,5S)-(+)-cis-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 
• 124623-51-4 (2S,5S)-(-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 
• 124623-50-3 (2S,5R)-(-)-cis-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 
• 124652-71-7 (2R,5R)-(+)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 

Relevant articles and documents

Method for high purity (+/-)-trans-4'-carboxyl cotinine

The invention discloses a method for a high purity (+/-)-trans-4'-carboxyl cotinine, which is characterized in that: mixing an ethanol solution of methylamine with 3-pyridylaldehyde to react; controlling the temperature to be between 25 and 30 DEG C, aging the reaction, and concentrating the solvent under reduced pressure to obtain an enimine intermediate I; adding the alkeneimine intermediate I into dimethylbenzene, adding succinic anhydride, and refluxing and aging; cooling the reaction solution to room temperature, and concentrating under reduced pressure to remove xylene; after the concentration is finished, adjusting the pH value of the concentrated solution to 8-9, extracting organic impurities by using dichloromethane, removing organic phase after layering to obtain white solid, sequentially washing with water, leaching with cold ethanol and drying in vacuum to obtain crude target product, and recrystallizing with ethanol to obtain the high purity (+/-)-trans-4'-carboxyl cotinine. According to the high purity (+/-)-trans-4'-carboxyl cotinine, the purity can reach more than 99 percent, and the total yield is more than 60 percent.

IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AS KINASE INHIBITORS

The present invention is intended to provide a compound or a pharmacologically acceptable salt thereof which is useful in the treatment of a tumor through its ROS1 kinase enzyme activity inhibitory effect and NTRK kinase enzyme inhibitory effect. The present invention provides a compound having an imidazo[1,2-b]pyridazine structure represented by the general formula (I) or a pharmacologically acceptable salt thereof, and a pharmaceutical composition comprising the compound. In the formula, R1, G, T, Y1, Y2, Y3, and Y4 are as defined herein.

Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction

A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogeni

Discovery of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as potent agonists of TGR5 via sequential combinatorial libraries

Optimization of a high-throughput screening hit led to the discovery of a new series of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as highly potent agonists of TGR5. This novel chemotype was rapidly developed through iterative combinatorial library synthesis. It was determined that in vitro agonist potency correlated with functional activity data from human peripheral blood monocytes.

Synthesis and evaluation of novel carbon-11 labeled oxopurine analogues for positron emission tomography imaging of translocator protein (18 kDa) in peripheral organs

To develop a PET ligand for imaging TSPO in peripheral organs, we designed three novel oxopurine analogues [11C]3a-c (LogD: 1.81-2.17) by introducing a pyridine ring in place of a benzene ring in the lead compound [11C]2 (LogD: 3.48). The desmethyl precursors 10 for radiosynthesis were synthesized by reacting glycine 7 with picolylamines 4, followed by hydrolysis and by Curtius rearrangement with diphenylphosphoryl azide. Methylation of 10a-c with methyl iodide produced unlabeled compounds 3a-c. The radiosynthesis of [11C]3a-c was performed by reacting 10a-c with [11C]methyl iodide. Compounds 3a-c displayed high or moderate in vitro binding affinities (Ki: 5-40 nM) for TSPO. PET with [ 11C]3a-c in rats showed high uptake in the lung, heart, and kidney, which are organs with high TSPO expression. Metabolite analysis with [ 11C]3a showed that radioactivity in these organs mainly corresponded with unchanged [11C]3a. PET with [11C]3a using a rat model of lung inflammation showed a significant signal in the lipopolysaccharide- treated lung.

Synthetic Study of the Highly Potent and Selective Anti-platelet Activating Factor Thiazolidin-4-one Agents and related Compounds

Stereoselective cyclo-condensation of α-sulfanylcarboxylic acids (or esters) 6 with N-methylarylimines 7 afforded the title compounds, 2-arylthiazolidin-4-ones, some of which exhibit highly potent anti-PAF activity.The reaction without added catalyst gave predominantly cis products, however, when titanium(IV) isopropoxide was added as catalyst trans products were predominantly formed.Allylation of 3-methyl-2-(3-pyridyl)thiazolidin-4-one 22 with allyl bromide using lithium amides gave the trans-5-allyl-2-(3-pyridyl)thiazolidin-4-one 23 with good selectivity.To study the stereostructure-activity relationship, the four optically active isomers of 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one 4 and 5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 5 were synthesized.The absolute configurations of compounds 4 and 5 were determined by X-ray analyses and 1H NMR measurements.Epimerization of the 5-position of compounds 4 and 5 was found to be effected by bases with high regioselectivity (>99percent), which was checked by a cross-over experiment using several optically active compounds.

Highly stereoselective synthesis of the anti-platelet activating factor, 4-thiazolidinones, using silyl derivatives of 2-mercaptoalkanoic acids

The cyclo-condensation of silyl 2-mercaptoalkanoates and arylmethyleneamines proceeded with high stereoselectivity to give alternatively both the cis- and trans-2,5-disubstituted 4-thiazolidinones, some of which are known as anti-platelet activating factor-active drugs. The use of the piperidine catalyst and no catalyst showed very high cis-stereoselectivity (cis/trans=10/1-50/1) during the reaction. On the other hand, the trans-selective reaction was promoted by Ti(O-i-Bu)4 and Al(O-s-Bu)3 catalysts (cis/trans=1/8-1/25). Both reactions were conducted with higher cis- and trans-selectivities as compared with those of the alkyl 2-mercaptoalkanoates under mild conditions. The cyclo-condensation using trimethylsilyl 2-(trimethylsilylthio)propionate and methyl 2-(trialkylsilylthio)propionates proceeded by the action of a catalytic amount (0.02 molar amount) of tetrabutylammonium fluoride with moderate cis-selectivity.