2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
[CAS# 1201186-54-0]

Identification

• Name: 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine
• Synonyms: 2-Bromo-5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazine; 2-Bromo-5-(4-methylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine
• Molecular Formula: C₁₃H₁₀BrN₃O₂S
• Molecular Weight: 352.21
• CAS Registry Number: 1201186-54-0
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=NC(=CN=C32)Br

Properties

• Solubility: Practically insoluble (0.067 g/L) (25 °C), Calc.^*
• Density: 1.68±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine is a significant compound in the field of organic chemistry, notable for its potential applications in medicinal chemistry and material science. This molecule features a pyrrolo[2,3-b]pyrazine core, substituted with a bromine atom and a tosyl group, which together impart unique chemical properties and biological activities.

The discovery of 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine emerged from research focused on developing new heterocyclic compounds with potential therapeutic applications. The pyrrolo[2,3-b]pyrazine framework is known for its diverse biological activities and ability to interact with various biological targets. The introduction of a bromine atom at the 2-position enhances the molecule’s reactivity and provides a handle for further chemical modifications. The tosyl group, located at the 5-position, serves both as a protecting group and as a functional group that can influence the molecule’s interactions with other chemical entities.

One of the primary applications of 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine is in the development of new pharmaceuticals. The compound’s structure makes it a valuable intermediate for synthesizing other bioactive molecules. The bromine atom can participate in various coupling reactions, allowing for the introduction of different functional groups that can modify the compound's biological activity. The tosyl group can be used to protect other functional groups during chemical transformations or to facilitate further functionalization.

The compound has shown promise in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling and regulation, and their dysregulation is associated with various diseases, including cancer. By incorporating the 2-bromo and 5-tosyl substitutions, researchers can design inhibitors with specific binding affinities for kinase targets, potentially leading to new treatments for cancer and other conditions where kinase activity is disrupted.

In addition to its role in drug development, 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine has applications in materials science. The molecule’s ability to undergo further chemical modifications makes it suitable for creating functionalized materials with specific properties. For example, it can be used to synthesize organic semiconductors or sensors due to its ability to form conjugated systems with desirable electronic properties. The versatility of the pyrrolo[2,3-b]pyrazine core enables the creation of materials with tailored functionalities for various applications in electronics and sensing technologies.

The synthesis of 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine involves the bromination of the pyrrolo[2,3-b]pyrazine core and the introduction of the tosyl group. This multi-step synthesis requires careful control of reaction conditions to ensure high yield and purity of the final product. The resulting compound can then be used as a versatile building block for further chemical transformations and applications.

Overall, 2-Bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazine represents a valuable addition to the toolkit of chemists working in drug discovery and materials science. Its unique structure and functional groups provide opportunities for developing new pharmaceuticals and advanced materials with specific properties. Continued research and exploration of this compound are expected to yield further insights into its potential applications and contribute to advancements in both fields.

References

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DOI: 10.1055/s-0041-1738394

2020. Tailor-made amino acid-derived pharmaceuticals approved by the FDA in 2019. Amino Acids.
DOI: 10.1007/s00726-020-02887-4

2020. Upadacitinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-21-0010