219727-28-3

Usage

InChI:InChI=1/C8H8ClN/c1-2-3-7-4-5-10-8(9)6-7/h2,4-6H,1,3H2

Upstream product

• 153034-86-7 2-chloro-4-iodopyridine 
• 106-95-6 allyl bromide 
• 73583-37-6 2-chloro-4-bromopyridine 
• 24850-33-7 allyltributylstanane 

Relevant academic research and scientific papers

AMINO-PYRIDINE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS

The invention provides certain amino-pyridine-containing compounds of the Formula (I) (I) or pharmaceutically acceptable salts thereof, wherein R3, R4, R5, R6, and the subscript n are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange

The reaction of heteroaryl iodides with i-PrMgBr (ca. 1.0 equiv) in THF provides the corresponding magnesiated heterocycles. Functional groups such as an ester, cyano, or chloride functions are tolerated in these new Grignard reagents if the exchange can be performed below -20 °C. This is the case for all heterocycles bearing electron-withdrawing groups or chelating functions facilitating the iodine-magnesium exchange. In many cases, the exchange can be extended to heteroaryl bromides, and a case of a chlorine-magnesium exchange is described with tetrachlorothiophene. This new preparation of functionalized heteroarylmagnesium compounds provides after reaction with various electrophiles a new entry to a broad range of polyfunctional pyridines, imidazoles, furanes, thiophenes, pyrroles, antipyrines, and uracil derivatives. The application of the halogenmagnesium exchange in the solid phase allows the performance of solid-phase synthesis, with potential applications for combinatorial chemistry.

Preparation of highly functionalized pyridylmagnesium reagents for the synthesis of polyfunctional pyridines

Functionalized iodopyridines bearing either a chloride, ester or nitrile function were converted to the corresponding organomagnesium derivatives at -40°C or -78°C by treatment with i-PrMgBr (1.1 equiv, 0.5 h, > 90% yield). The resulting functionalized Grignard reagents react with aldehydes, TosCN directly or with allylic bromides and benzoyl chloride after transmetalation with CuCN leading to polyfunctional pyridines.