444120-91-6 Usage
Description
2-Chloropyridine-5-boronic acid is an organic compound with the chemical formula C5H4BClNO2. It is a derivative of pyridine, a heterocyclic aromatic compound, and features a boronic acid group attached to the 5-position and a chlorine atom at the 2-position. 2-Chloropyridine-5-boronic acid is known for its reactivity and versatility in organic synthesis, making it a valuable intermediate in the preparation of various biologically active molecules and pharmaceuticals.
Uses
Used in Pharmaceutical Industry:
2-Chloropyridine-5-boronic acid is used as a key intermediate in the synthesis of biologically significant 3-arylcoumarins. These compounds are prepared through the Suzuki reaction with 3-chlorocoumarin, a reaction that facilitates the formation of carbon-carbon bonds between the boronic acid and the halide-containing coumarin. The resulting 3-arylcoumarins possess valuable pharmacological properties and are used in the development of drugs targeting various diseases.
Used in Steroid Chemistry:
In the field of steroid chemistry, 2-Chloropyridine-5-boronic acid serves as a substrate for the synthesis of 11-(pyridinylphenyl)steroids. These steroids exhibit a unique profile as progesterone agonists or antagonists, depending on their structural features. The incorporation of the pyridine moiety through the use of 2-Chloropyridine-5-boronic acid allows for the fine-tuning of the biological activity of these steroids, making them potential candidates for hormone-related therapies.
Used in the Synthesis of Pyridine Derivatives:
2-Chloropyridine-5-boronic acid is also utilized as a substrate in the preparation of α-secondary and tertiary pyridines. These pyridines are synthesized through the reaction of pyridotriazoles with boronic acids, a process that involves the formation of new carbon-carbon bonds. The resulting pyridine derivatives find applications in various fields, including medicinal chemistry, as they can be further functionalized to create novel bioactive molecules.
Used in Palladium-Catalyzed α-Arylation:
In the realm of palladium-catalyzed reactions, 2-Chloropyridine-5-boronic acid plays a crucial role as a substrate in the α-arylation of saturated cyclic amines and N-methyl amines. This reaction allows for the direct arylation of amines with the pyridine moiety, providing a convenient and efficient method for the synthesis of a wide range of nitrogen-containing heterocycles. These heterocycles are valuable building blocks in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Check Digit Verification of cas no
The CAS Registry Mumber 444120-91-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,4,4,1,2 and 0 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 444120-91:
(8*4)+(7*4)+(6*4)+(5*1)+(4*2)+(3*0)+(2*9)+(1*1)=116
116 % 10 = 6
So 444120-91-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H5BClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H
444120-91-6Relevant articles and documents
METHOD FOR PRODUCING 6-HALOGENO-3-ARYLPYRIDINE DERIVATIVE
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Page/Page column 10, (2010/09/17)
[Problem] The present invention provides an industrially advantageous production method of a 6-halogeno-3-arylpyridine derivative in which cryogenic condition is not required, production step is short, and an isomer difficult to be separated is not produced as a by-product. [Solution] A production method of a 6-halogeno-3-arylpyridine derivative represented by the general formula (III) comprising: the first step reacting a 2, 5-dihalogenopyridine derivative represented by the general formula (I) with a magnesiation reagent; and the second step reacting the product obtained from the above-described first step, in the presence of a palladium compound, with a halogenoaryl derivative represented by the general formula (II).
SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
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Page/Page column 93, (2010/02/12)
Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.
An efficient route to 6-(het)aryl-2-methyl-2,3-dihydro-1H-pyridin-4-ones as potential nAChRs ligands
Leflemme, Nicolas,Dallemagne, Patrick,Rault, Sylvain
, p. 4861 - 4865 (2007/10/03)
A new efficient pathway to synthesise 6-(het)aryl-2-methyl-2,3-dihydro-1H- pyridin-4-ones is described. This reaction sequence involved, as a key step, a Suzuki cross-coupling reaction between various boronic acids and an 6-iodo-2,3-dihydropyridin-4-one. A final deprotecting step furnished the attempted products.
