Production Method 1

6980-08-1

942947-95-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  1 h, 80 °C

Reference

Preparation of substituted 1H-imidazo[4,5-b]pyridin-2(3H)-ones and their use as GluN2B receptor modulators

, World Intellectual Property Organization, , ,

Production Method 2

942947-94-6

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  < 10 °C; 15 min, 5 - 10 °C; 55 °C
1.2 Reagents: Nitric acid Solvents: Water ;  55 - 60 °C; 30 min, 55 °C; 55 °C → rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 7

Reference

Imidazo[4,5-b]pyridine Derivatives As Inhibitors of Aurora Kinases: Lead Optimization Studies toward the Identification of an Orally Bioavailable Preclinical Development Candidate

Bavetsias, Vassilios; Large, Jonathan M.; Sun, Chongbo; Bouloc, Nathalie; Kosmopoulou, Magda; et al, Journal of Medicinal Chemistry, 2010, 53(14), 5213-5228

Production Method 3

1976019-50-7

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  rt; 2.5 h, 40 °C; 40 °C → rt
1.2 Reagents: Water ;  neutralized, cooled

Reference

2-Phenyl-3H-imidazo[4,5-b]pyridine derivatives as inhibitors or mammalian tyrosine kinase ROR1 activity and their preparation

, World Intellectual Property Organization, , ,

Production Method 4

942947-95-7

Reaction Conditions

Reference

Preparation of 2,3-diamino-4-bromopyridine

, China, , ,

Production Method 5

6980-08-1

942947-95-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  1 h, 80 °C

Reference

Preparation of imidazopyridines as inhibitors of aurora kinase and/or FLT3

, World Intellectual Property Organization, , ,

Production Method 6

6980-08-1

942947-95-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  1 h, 80 °C

Reference

Optimization of Imidazo[4,5-b]pyridine-Based Kinase Inhibitors: Identification of a Dual FLT3/Aurora Kinase Inhibitor as an Orally Bioavailable Preclinical Development Candidate for the Treatment of Acute Myeloid Leukemia

Bavetsias, Vassilios; Crumpler, Simon; Sun, Chongbo; Avery, Sian; Atrash, Butrus; et al, Journal of Medicinal Chemistry, 2012, 55(20), 8721-8734

Production Method 7

942947-94-6

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid ;  0 °C → 55 °C; 1 h, 55 °C
1.2 Reagents: Sodium hydroxide ;  pH 7

Reference

Imidazopyridine derivative and pharmaceutical composition comprising same as active ingredient

, Korea, , ,

Production Method 8

942947-94-6

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  0 °C; 0 °C → 55 °C; 1 h, 55 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7

Reference

Preparation of imidazopyridine derivative as protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 9

1976019-50-7

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  rt; 2.5 h, 40 °C

Reference

2-Phenylimidazo[4,5-B]pyridin-7-amine derivatives used as inhibitors of mammalian tyrosine kinase ROR1 activity and their preparation

, United States, , ,

Production Method 10

942947-94-6

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  -5 °C
1.2 Reagents: Fuming nitric acid ;  5 min, < 0 °C; 2 h, 0 °C → 50 °C; 1 h, 50 °C
1.3 Reagents: Water ;  cooled
1.4 Reagents: Ammonia ;  pH 7.3

Reference

Discovery and analgesic evaluation of 8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione as a novel potent D-amino acid oxidase inhibitor

Xie, Dongsheng; Lu, Jun; Xie, Jin; Cui, Junjun; Li, Teng-Fei; et al, European Journal of Medicinal Chemistry, 2016, 117, 19-32

Production Method 11

942947-94-6

942947-95-7

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  15 min, -10 °C
1.2 Reagents: Nitric acid Solvents: Water ;  55 - 60 °C; 30 min, 55 °C; 55 °C → rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 7, cooled

Reference

Preparation of imidazopyridines as enzyme inhibitors, especially Aurora kinase inhibitors, for treating cell proliferative diseases

, World Intellectual Property Organization, , ,

5-bromo-4-chloro-3-nitro-pyridin-2-amine Raw materials

• 2-Amino-4-chloro-3-nitropyridine
• 5-Bromo-4-chloropyridin-2-amine
• 2-Pyridinamine, 5-bromo-4-chloro-N-nitro-

5-bromo-4-chloro-3-nitro-pyridin-2-amine Preparation Products

• 5-bromo-4-chloro-3-nitro-pyridin-2-amine (942947-95-7)

• 1. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 2. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
• 3. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 4. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 5. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
  Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847

Introduction to 5-bromo-4-chloro-3-nitro-pyridin-2-amine (CAS No. 942947-95-7)

5-bromo-4-chloro-3-nitro-pyridin-2-amine, identified by the Chemical Abstracts Service Number (CAS No.) 942947-95-7, is a specialized heterocyclic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound belongs to the pyridine family, a class of nitrogen-containing heterocycles that are widely recognized for their diverse biological activities and structural versatility. The presence of multiple substituents, including bromine, chlorine, and nitro groups, imparts unique reactivity and functional properties, making it a valuable intermediate in synthetic chemistry.

The structural configuration of 5-bromo-4-chloro-3-nitro-pyridin-2-amine consists of a pyridine ring substituted at the 2-amino, 3-nitro, 4-chloro, and 5-bromo positions. This specific arrangement of functional groups enhances its utility as a building block in the synthesis of more complex molecules. The amino group at the 2-position provides a nucleophilic center for further functionalization, while the nitro group introduces electrophilic reactivity and potential electron-withdrawing effects that can influence the electronic properties of the molecule.

In recent years, there has been a growing interest in exploring the pharmacological potential of pyridine derivatives. The combination of halogenated aromatic rings with nitro substituents has been particularly studied for their ability to modulate biological pathways. For instance, related compounds have shown promise in inhibiting enzymes involved in cancer metabolism and inflammation. The specific substitution pattern of 5-bromo-4-chloro-3-nitro-pyridin-2-amine makes it a candidate for further investigation in these areas.

One of the most compelling aspects of this compound is its role as a precursor in the synthesis of biologically active molecules. Researchers have leveraged its reactive sites to develop novel scaffolds for drug discovery. The bromo and chloro groups, in particular, are frequently utilized in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are essential for constructing carbon-carbon bonds in complex organic molecules. These reactions allow for the introduction of aryl or alkyl groups at various positions on the pyridine core, expanding the chemical space available for drug design.

The nitro group in 5-bromo-4-chloro-3-nitro-pyridin-2-amine also plays a crucial role in its reactivity. Nitro compounds are known for their ability to undergo reduction to form amine derivatives, which can be further modified to produce pharmacologically relevant structures. This transformation is particularly useful in generating amino acid mimetics or other bioactive peptides that interact with biological targets.

Recent studies have highlighted the importance of halogenated pyridines in medicinal chemistry. The presence of bromine and chlorine atoms not only facilitates further functionalization but also influences the metabolic stability and bioavailability of derived compounds. For example, halogenated aromatic compounds have been shown to exhibit improved binding affinities to protein targets due to their ability to engage multiple interaction sites simultaneously.

In addition to its pharmaceutical applications, 5-bromo-4-chloro-3-nitro-pyridin-2-amine has potential uses in agrochemical research. Pyridine derivatives are well-documented for their role as intermediates in herbicides and pesticides. The structural features of this compound make it a suitable candidate for developing new agrochemical agents that target specific enzymatic pathways in pests while maintaining environmental safety.

The synthesis of 5-bromo-4-chloro-3-nitro-pyridin-2-amine typically involves multi-step organic transformations starting from commercially available pyridine precursors. Key steps often include halogenation reactions at specified positions on the ring followed by nitration. Careful control of reaction conditions is essential to achieve high yields and purity, as side reactions can lead to undesired byproducts.

From an industrial perspective, the production scalability of this compound is an important consideration. Advances in catalytic methods have enabled more efficient synthesis routes, reducing costs and improving sustainability. Green chemistry principles are increasingly being applied to minimize waste and hazardous byproducts during manufacturing processes.

The analytical characterization of 5-bromo-4-chloro-3-nitro-pyridin-2-amine relies on modern spectroscopic techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC). These methods provide detailed information about the molecular structure and purity of the compound, ensuring its suitability for downstream applications.

In conclusion,5-bromo-4-chloro-3-nitro-pyridin-2-amineseems poised to play a significant role in future research endeavors within pharmaceuticals and agrochemicals due to its versatile structural features and reactivity profile. Continued exploration into its synthetic applications will likely uncover novel derivatives with enhanced biological activities, contributing to advancements across multiple scientific disciplines.

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