Production Method 1

63996-36-1

73183-34-3

908350-80-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  14 h, rt → 85 °C

Reference

Iridium(III) Complex Radical and Corresponding Ligand Radical Functionalized by a Tris(2,4,6-trichlorophenyl)methyl Unit: Synthesis, Structure, and Photophysical Properties

Liu, Xinyu; Wu, Meng; Zeng, Ruoqi; Li, Gang; Li, Qiuxia; et al, Inorganic Chemistry, 2022, 61(51), 20942-20948

Production Method 2

73183-34-3

908350-80-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Bis(acetylacetonato)nickel ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dimethyl-, chloride (1… Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C

Reference

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

Pein, Wesley L. ; Wiensch, Eric M.; Montgomery, John, Organic Letters, 2021, 23(12), 4588-4592

Production Method 3

73183-34-3

4467-06-5

908350-80-1

Reaction Conditions

1.1 Reagents: N-Hydroxyphthalimide ,  tert-Butyl nitrite Catalysts: Lithium bromide Solvents: Acetonitrile ;  48 h, 80 °C
1.2 Catalysts: 1,1-Dimethylethyl 3-pyridinecarboxylate Solvents: (Trifluoromethyl)benzene ;  15 h, 110 °C

Reference

Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Dai, Peng-Fei; Ning, Xiao-Shan; Wang, Hua; Cui, Xian-Chao; Liu, Jie; et al, Angewandte Chemie, 2019, 58(16), 5392-5395

Production Method 4

63996-36-1

73183-34-3

908350-80-1

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethylformamide ;  24 h, 80 °C

Reference

Spiro-Linked Hyperbranched Architecture in Electrophosphorescent Conjugated Polymers for Tailoring Triplet Energy Back Transfer

Shao, Shiyang; Ma, Zhihua; Ding, Junqiao; Wang, Lixiang; Jing, Xiabin; et al, Advanced Materials (Weinheim, 2012, 24(15), 2009-2013

Production Method 5

51035-40-6

73183-34-3

908350-80-1

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: 1,4-Dioxane ;  24 h, 60 °C

Reference

Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation

Liu, Xiaojie; Xu, Biping; Su, Weiping, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 6

14874-70-5

73183-34-3

908350-80-1

Reaction Conditions

1.1 Catalysts: Dimanganese decacarbonyl Solvents: Acetonitrile ;  2 h, rt

Reference

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Firth, James D.; Hammarback, L. Anders; Burden, Thomas J.; Eastwood, Jonathan B.; Donald, James R.; et al, Chemistry - A European Journal, 2021, 27(12), 3979-3985

Production Method 7

908350-80-1

Reaction Conditions

1.1 Reagents: Ammonium acetate ,  Azidotrimethylsilane ,  Oxygen Catalysts: Cobalt(II) acetylacetonate ,  Bis[2-(diphenylphosphino)phenyl] ether Solvents: 1,2-Dimethoxyethane ,  Water ;  24 h, 80 °C

Reference

Cobalt-Catalyzed Nitrogen Atom Insertion in Arylcycloalkenes

Wang, Juanjuan; Lu, Hong ; He, Yi; Jing, Chunxiu; Wei, Hao, Journal of the American Chemical Society, 2022, 144(49), 22433-22439

Production Method 8

73183-34-3

908350-80-1

Reaction Conditions

1.1 Reagents: Lithium tert-butoxide Catalysts: Bis(acetylacetonato)nickel ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dimethyl-, chloride (1… Solvents: Cyclopentyl methyl ether ;  16 h, 100 °C

Reference

Nickel-catalyzed ipso-borylation of silyloxyarenes via C-O bond activation

Pein, Wesley L.; Wiensch, Eric M.; Montgomery, John, ChemRxiv, 2021, 1, 1-6

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine Raw materials

• Borate(1-),tetrafluoro-
• 4-(Pyridin-2-yl)phenol
• 2-(4-Bromophenyl)pyridine
• Bis(pinacolato)diborane
• 2-(p-Tolyl)pyridine

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine Preparation Products

• 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (908350-80-1)

• 1. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 2. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
  Adeline Huiling Loo,Alessandra Bonanni,Martin Pumera Analyst, 2013,138, 467-471
• 3. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 4. An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane?
  Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. Yeste J. Mater. Chem. A, 2019,7, 8993-9003
• 5. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829

Professional Introduction to Compound with CAS No. 908350-80-1 and Product Name: 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

The compound with the CAS number 908350-80-1 and the product name 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine represents a significant advancement in the field of pharmaceutical chemistry. This compound has garnered considerable attention due to its unique structural features and potential applications in drug development. The presence of a tetramethyl-1,3,2-dioxaborolan-2-yl moiety and a phenyl group attached to a pyridine core suggests a versatile scaffold that could be exploited for various biochemical interactions.

Recent research in medicinal chemistry has highlighted the importance of boron-containing compounds in the design of novel therapeutic agents. The tetramethyl-1,3,2-dioxaborolan-2-yl group is particularly noteworthy as it serves as an excellent handle for cross-coupling reactions, which are fundamental in constructing complex molecular architectures. This feature makes the compound a valuable intermediate in synthetic organic chemistry, enabling the facile preparation of more intricate derivatives. Such derivatives could potentially exhibit enhanced pharmacological properties compared to their parent structures.

The pyridine core of the molecule is another critical feature that contributes to its pharmacological relevance. Pyridine derivatives are well-documented for their role in various biological processes and have been extensively explored in the development of drugs targeting neurological disorders, cardiovascular diseases, and infectious diseases. The combination of a pyridine ring with a phenyl group and a boronate ester moiety creates a multifunctional platform that can be further modified to tailor specific biological activities. This versatility is particularly advantageous in drug discovery pipelines where rapid iteration and optimization are essential.

One of the most exciting aspects of this compound is its potential application in the development of small-molecule inhibitors. The phenyl group attached to the boronate ester can be readily functionalized through palladium-catalyzed cross-coupling reactions, allowing for the introduction of diverse substituents that modulate binding affinity and selectivity. Such modifications are crucial for improving drug efficacy and minimizing off-target effects. In particular, recent studies have demonstrated that boronate esters can serve as effective tools for covalent inhibition of enzyme targets, offering a promising strategy for developing highly potent and selective inhibitors.

Furthermore, the compound's structural features align well with current trends in drug design aimed at improving solubility and bioavailability. The presence of polar functional groups such as the boronate ester and the pyridine nitrogen provides opportunities for hydrogen bonding interactions with biological targets. These interactions can enhance binding affinity while also improving pharmacokinetic profiles. Additionally, the tetramethyl substitution pattern on the dioxaborolane ring contributes to steric stabilization, which can prevent unwanted conformations that might reduce bioactivity.

In the context of modern drug discovery, computational modeling plays an increasingly important role in guiding synthetic strategies and predicting biological activity. The structural features of this compound make it an attractive candidate for molecular docking studies aimed at identifying potential binding pockets in target proteins. Such studies can provide valuable insights into how the compound interacts with its biological counterpart and can guide further optimization efforts. By leveraging computational tools alongside experimental data, researchers can accelerate the discovery process and increase the likelihood of identifying lead compounds with favorable pharmacological properties.

Recent advancements in synthetic methodologies have also contributed to the growing interest in boron-containing compounds like this one. Techniques such as transition-metal-catalyzed borylation reactions have made it possible to introduce boronate esters into complex molecular frameworks with high efficiency and selectivity. These methods have enabled chemists to access novel scaffolds that were previously difficult or impossible to synthesize. As a result, compounds like this one are being explored for their potential applications in various therapeutic areas.

The pharmaceutical industry has long recognized the importance of innovative molecular architectures in driving therapeutic breakthroughs. The unique combination of structural features found in this compound exemplifies how careful molecular design can lead to novel entities with promising biological activity. By integrating insights from synthetic chemistry, computational biology, and pharmacology, researchers can develop next-generation drugs that address unmet medical needs more effectively than ever before.

In conclusion,2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine represents a compelling example of how structural innovation can drive progress in drug discovery. Its versatile framework offers numerous opportunities for further modification and optimization, making it a valuable asset in the quest for new therapeutic agents. As research continues to uncover new applications for boron-containing compounds, this molecule is poised to play an important role in shaping the future of pharmaceutical chemistry.

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