59409-80-2

Usage

Uses

Used in Organic Synthesis:
2-Bromo-6-(trimethylsilyl)pyridine is used as a reagent for the modification of functional groups on aromatic compounds. The presence of the bromine atom allows it to participate in various substitution reactions, while the trimethylsilyl group can act as a protecting group for alcohols and amines.
Used in Pharmaceutical Industry:
2-Bromo-6-(trimethylsilyl)pyridine is used as a chemical building block in the development of pharmaceuticals. Its unique structure and reactivity make it a valuable component in the synthesis of new drug molecules.
Used in Agrochemical Industry:
In the agrochemical sector, 2-bromo-6-(trimethylsilyl)pyridine is utilized as a key intermediate in the synthesis of various agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Materials Science:
2-Bromo-6-(trimethylsilyl)pyridine also finds applications in materials science, where it can be incorporated into the design and synthesis of new materials with specific properties, such as improved stability or enhanced performance in various applications.

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 75-77-4 chloro-trimethyl-silane 
• 109-04-6 2-bromo-pyridine 
• 693-04-9 butyl magnesium bromide 

Downstream Products

• 1310584-61-2 2-(1-hydroxy-1-phenylethyl)-6-trimethylsilylpyridine 

Relevant academic research and scientific papers

Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems

A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.

Flow microreactor synthesis of disubstituted pyridines from dibromopyridines via Br/Li exchange without using cryogenic conditions

A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed. By using a short residence time and efficient temperature control, the cryogenic conditions required for conventional batch macro processes can be avoided. Sequential introduction of two different electrophiles into dibromopyridines has been achieved using an integrated flow microreactor system composed of four micromixers and four microtube reactors, to obtain disubstituted pyridine compounds.

Method of converting functional group through halogen-metal exchange reaction

A method by which a halogen atom of a halogen compound can be efficiently replaced with an electrophilic group. Also provided are: a reagent for converting a functional group through a halogen-metal exchange reaction, characterized by comprising either a mixture of a magnesium compound represented by the formula R1—Mg—X (I) (wherein R1 represents a halogen atom or an optionally substituted hydrocarbon residue; and X1 represents a halogen atom) and an organolithium compound represented by the formula R2—Li (II) (wherein R2 represents an optionally substituted hydrocarbon residue) or a product of the reaction of the magnesium compound with the organolithium compound; and a process for producing with the reagent a compound in which a halogen atom of a halogen compound has been replaced with an electrophilic group.

Asymmetric synthesis of β-pyridyl-β-amino acid derivatives

The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee.

Regiocontrolled deprotonative-zincation of bromopyridines using aminozincates

Regiochemistry in the deprotonation of bromopyridines was found to be greatly influenced by the choice of metal amide base, and DA-zincate and TMP-zincate turned out to be excellent complementary practical agents for regioselective metalation of bromopyri

New syntheses of substituted pyridines via bromine-magnesium exchange

Bromine-magnesium exchange using iPrMgCl in THF at room temperature on 2-, 3- and 4-bromopyridines allowed the synthesis of various functionalized pyridines. The methodology was successfully used for the synthesis of 4- azaxanthone. Moreover, single exchange reactions observed on 2,6-, 3,5-, 2,3- and 2,5-dibromopyridines, with complete regioselectivity in the case of 2,3- and 2,5-dibromopyridines, afforded substituted bromopyridines, which were then involved in a second exchange step to provide difunctionalized pyridines. (C) 2000 Elsevier Science Ltd.