Production Method 1

19798-81-3

89284-11-7

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Lithium perchlorate Solvents: Acetic acid ,  Acetonitrile ;  8 h, 25 °C

Reference

Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions

Wu, Yanwei; Xu, Shanghui; Wang, Hong; Shao, Dongxu; Qi, Qiqi; et al, Journal of Organic Chemistry, 2021, 86(22), 16144-16150

Production Method 2

19798-81-3

89284-11-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dichloromethane ;  rt; 6 h, rt
1.2 Reagents: Water ;  rt

Reference

Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis

Che, Jinxin; Jin, Zegao; Yan, Fangjie; You, Jieqiong; Xie, Jiangfeng; et al, Journal of Medicinal Chemistry, 2021, 64(12), 8621-8643

5,6-Dibromopyridin-2-amine Raw materials

• 6-Bromopyridin-2-amine

5,6-Dibromopyridin-2-amine Preparation Products

• 5,6-Dibromopyridin-2-amine (89284-11-7)

• 1. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 2. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804
• 3. An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions?
  Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng Cao J. Mater. Chem. A, 2014,2, 7662-7665
• 4. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 5. An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme?
  Yang Chen,Di Zhou,Zheyi Meng,Jin Zhai Chem. Commun., 2016,52, 10020-10023

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines Polyhalopyridines
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Research Brief on 5,6-Dibromopyridin-2-amine (CAS: 89284-11-7): Recent Advances and Applications in Chemical Biology and Pharmaceutical Research

5,6-Dibromopyridin-2-amine (CAS: 89284-11-7) is a halogenated pyridine derivative that has garnered significant attention in recent years due to its versatile applications in medicinal chemistry and chemical biology. This compound serves as a crucial building block for the synthesis of various pharmacologically active molecules, particularly in the development of kinase inhibitors and antimicrobial agents. Recent studies have highlighted its potential in targeted drug design and as a scaffold for fragment-based drug discovery (FBDD) approaches.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 5,6-Dibromopyridin-2-amine as a precursor for the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The researchers utilized the bromine substituents for efficient palladium-catalyzed cross-coupling reactions, enabling rapid diversification of the pyridine core. The resulting compounds showed promising activity against both wild-type and C481S mutant BTK, with IC50 values in the low nanomolar range, suggesting potential applications in overcoming ibrutinib resistance in B-cell malignancies.

In the field of antimicrobial research, a recent publication in Bioorganic & Medicinal Chemistry Letters (2024) reported the development of new quinolone-pyridine hybrids using 5,6-Dibromopyridin-2-amine as a key intermediate. These hybrids exhibited potent activity against drug-resistant strains of Staphylococcus aureus and Mycobacterium tuberculosis, with several analogs showing improved selectivity indices compared to current frontline antibiotics. The study emphasized the importance of the 2-amino group in enhancing bacterial membrane penetration while maintaining low cytotoxicity against mammalian cells.

From a synthetic chemistry perspective, advances in continuous flow chemistry have significantly improved the production scalability of 5,6-Dibromopyridin-2-amine. A 2023 Chemical Engineering Journal paper described an optimized continuous process that achieved 92% yield with >99% purity, addressing previous challenges in large-scale production. This development is particularly relevant for pharmaceutical companies looking to incorporate this building block into their drug discovery pipelines.

Emerging applications in chemical biology include the use of 5,6-Dibromopyridin-2-amine as a versatile tag for protein labeling and bioconjugation. Recent work published in ACS Chemical Biology (2024) demonstrated its effectiveness in creating stable protein-polymer conjugates through selective modification of cysteine residues, opening new possibilities for therapeutic protein engineering and targeted drug delivery systems.

The safety profile and ADME properties of derivatives containing the 5,6-Dibromopyridin-2-amine scaffold have been systematically investigated in several recent preclinical studies. While the parent compound shows moderate metabolic stability, strategic modifications at the 2-amino position have been shown to significantly improve pharmacokinetic parameters without compromising target engagement, as reported in a 2024 European Journal of Medicinal Chemistry paper.

Looking forward, the unique structural features of 5,6-Dibromopyridin-2-amine continue to inspire innovative applications across multiple therapeutic areas. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) designs and as a core structure for developing allosteric modulators of challenging drug targets. The compound's commercial availability from multiple specialty chemical suppliers and its well-established synthetic routes ensure its continued importance in pharmaceutical research and development.

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