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• 2. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
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Professional Introduction to 2-Bromo-6-(tert-butoxy)pyridine (CAS No. 949160-14-9)

2-Bromo-6-(tert-butoxy)pyridine, with the chemical formula C₉H₁₃BrN, is a significant compound in the realm of pharmaceutical and agrochemical research. This heterocyclic aromatic brominated derivative has garnered considerable attention due to its versatile applications in synthetic chemistry and medicinal chemistry. The presence of both a bromine substituent and a tert-butoxy group on the pyridine ring imparts unique reactivity, making it a valuable intermediate in the synthesis of various biologically active molecules.

The compound's molecular structure, characterized by a pyridine core with bromine at the 2-position and a tert-butoxy group at the 6-position, facilitates its use in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are pivotal in constructing complex organic molecules, including pharmaceuticals and agrochemicals. The electron-withdrawing nature of the bromine atom enhances the electrophilicity of the pyridine ring, while the sterically hindered tert-butoxy group provides stability during synthetic transformations.

In recent years, 2-Bromo-6-(tert-butoxy)pyridine has been employed in the development of novel therapeutic agents. For instance, its incorporation into pyridine-based scaffolds has led to the discovery of compounds with potential antimicrobial and anti-inflammatory properties. Researchers have leveraged its reactivity to introduce diverse functional groups, enabling the creation of libraries of derivatives for high-throughput screening.

One notable application of this compound is in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is associated with various diseases, including cancer. By modifying the pyridine core with electron-deficient substituents like bromine, chemists can design inhibitors that target specific kinases with high selectivity. The tert-butoxy group helps to fine-tune the pharmacokinetic properties of these inhibitors, improving their solubility and metabolic stability.

The agrochemical industry has also benefited from the use of 2-Bromo-6-(tert-butoxy)pyridine. Its derivatives have been explored as intermediates in the synthesis of herbicides and fungicides. These compounds exhibit potent activity against a range of plant pathogens, offering farmers effective solutions for crop protection. The structural features of this compound allow for modifications that enhance its bioavailability and environmental compatibility.

Advances in computational chemistry have further enhanced the utility of 2-Bromo-6-(tert-butoxy)pyridine. Molecular modeling studies have provided insights into its interactions with biological targets, aiding in the rational design of more effective drugs. Additionally, machine learning algorithms have been trained on datasets containing this compound to predict its reactivity and optimize synthetic routes.

The future prospects for 2-Bromo-6-(tert-butoxy)pyridine are promising, with ongoing research exploring its potential in drug discovery and material science. As our understanding of molecular interactions deepens, new applications for this versatile compound are likely to emerge. Its role as a building block in synthetic chemistry ensures that it will remain a cornerstone in the development of innovative chemical entities for years to come.

• 463336-87-0(2-Bromo-6-isopropoxypyridine)
• 891842-83-4(Pyridine, 2-bromo-6-(2-methylpropoxy)-)
• 891842-82-3(2-Bromo-6-propoxypyridine)
• 56446-70-9(Pyridine, 2,2'-[1,2-ethanediylbis(oxy)]bis[6-bromo-)
• 4645-11-8(2-Bromo-6-ethoxypyridine)
• 1092848-28-6(2-Bromo-6-butoxypyridine)
• 891842-80-1(Pyridine, 2-bromo-6-(cyclobutyloxy)-)
• 61463-67-0(Ethanol, 2-[(6-bromo-2-pyridinyl)oxy]-)
• 56446-68-5(Ethanol, 2-[2-[(6-bromo-2-pyridinyl)oxy]ethoxy]-)
• 56446-69-6(PYRIDINE, 2,2'-[OXYBIS(2,1-ETHANEDIYLOXY)]BIS[6-BROMO-)