Production Method 1

5332-24-1

898559-23-4

Reaction Conditions

1.1 Reagents: Magnesate(1-), dichloro(2,2,6,6-tetramethylpiperidinato)-, lithium (1:1) Solvents: Tetrahydrofuran ;  0.3 h, -30 °C
1.2 Reagents: Iodine Solvents: Tetrahydrofuran
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  -30 °C
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Mixed Mg/Li amides of the type R2NMgCl·LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds

Krasovskiy, Arkady; Krasovskaya, Valeria; Knochel, Paul, Angewandte Chemie, 2006, 45(18), 2958-2961

Production Method 2

5332-24-1

898559-23-4

Reaction Conditions

1.1 Reagents: Zincate(1-), trichloro-, lithium Solvents: Tetrahydrofuran ;  20 min, 25 °C
1.2 Reagents: Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) Solvents: Tetrahydrofuran ;  25 °C → -70 °C; 0 °C; 20 min, 0 °C
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  30 min, 25 °C

Reference

Selective Functionalization of Benzo-Fused N-Heterocycles by Using In Situ Trapping Metalations

Nishimura, Rodolfo H. V.; Murie, Valter E.; Vessecchi, Ricardo; Clososki, Giuliano C., ChemistrySelect, 2020, 5(36), 11106-11111

Production Method 3

898559-23-4

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetonitrile ;  5 h, reflux

Reference

A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions

Boganyi, Borbala; Kaman, Judit, Tetrahedron, 2013, 69(45), 9512-9519

Production Method 4

5332-24-1

898559-23-4

Reaction Conditions

1.1 Reagents: Piperidine, 2,2,6,6-tetramethyl-, zirconium(4+) salt (4:1) Solvents: Tetrahydrofuran ;  -20 °C; 45 min, -20 °C
1.2 Reagents: Iodine ;  1 h, -20 - 0 °C
1.3 Reagents: Sodium thiosulfate Solvents: Water

Reference

tmp4Zr: an atom-economical base for the metalation of functionalized arenes and heteroarenes

Jeganmohan, Masilamani; Knochel, Paul, Angewandte Chemie, 2010, 49(45), 8520-8524

3-bromo-2-iodoquinoline Raw materials

• 3-Bromoquinoline

3-bromo-2-iodoquinoline Preparation Products

• 3-bromo-2-iodoquinoline (898559-23-4)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Haloquinolines

Professional Introduction to 3-bromo-2-iodoquinoline (CAS No: 898559-23-4)

3-bromo-2-iodoquinoline (CAS No: 898559-23-4) is a highly versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, characterized by its bromo and iodo substituents on a quinoline backbone, serves as a crucial intermediate in the synthesis of various biologically active molecules. Its unique structural framework makes it an attractive scaffold for designing novel therapeutic agents targeting a range of diseases.

The quinoline core is a well-established motif in medicinal chemistry, with numerous derivatives exhibiting antimicrobial, antimalarial, and anticancer properties. The introduction of halogen atoms at specific positions on the quinoline ring enhances its reactivity, enabling further functionalization through cross-coupling reactions such as Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings. These reactions are pivotal in constructing complex molecular architectures, making 3-bromo-2-iodoquinoline a valuable building block for drug discovery efforts.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors for kinases and other enzymes involved in cancer progression. 3-bromo-2-iodoquinoline has emerged as a key intermediate in the synthesis of kinase inhibitors due to its ability to undergo sequential halogen-metal exchange followed by palladium-catalyzed cross-coupling reactions. Such transformations allow for the introduction of diverse pharmacophores, leading to the development of potent and selective inhibitors with therapeutic potential.

Moreover, the compound has found applications in the synthesis of quinoline-based antiviral agents. The bromo and iodo substituents provide handles for further derivatization, enabling the construction of molecules capable of interfering with viral replication cycles. Recent studies have highlighted the use of 3-bromo-2-iodoquinoline in generating quinoline derivatives with inhibitory activity against viruses such as HIV and hepatitis C. These findings underscore the compound's significance as a precursor in antiviral drug development.

The reactivity of 3-bromo-2-iodoquinoline also extends to its use in material science applications. Quinoline derivatives are known for their luminescent properties, making them suitable candidates for organic light-emitting diodes (OLEDs) and other optoelectronic devices. The halogen atoms on the quinoline ring facilitate further functionalization, allowing for the tuning of electronic and optical properties. This has led to increased interest in exploring 3-bromo-2-iodoquinoline as a precursor for developing novel materials with enhanced performance characteristics.

From a synthetic chemistry perspective, 3-bromo-2-iodoquinoline offers unique opportunities for exploring new methodologies and reaction pathways. The presence of both bromo and iodo substituents makes it an ideal candidate for studying halogen-metal exchange reactions and their applications in synthetic transformations. Such studies not only contribute to the advancement of organic chemistry but also provide insights into developing more efficient synthetic strategies for complex molecular architectures.

The pharmaceutical industry has been particularly keen on leveraging the versatility of 3-bromo-2-iodoquinoline for drug discovery initiatives. Its role as a key intermediate in synthesizing kinase inhibitors underscores its importance in oncology research. Additionally, its utility in generating antiviral agents highlights its broader applicability across different therapeutic areas. As drug development continues to evolve, compounds like 3-bromo-2-iodoquinoline are expected to play an increasingly significant role in addressing unmet medical needs.

In conclusion, 3-bromo-2-iodoquinoline (CAS No: 898559-23-4) is a multifaceted compound with far-reaching implications in pharmaceutical chemistry and material science. Its unique structural features and reactivity make it an indispensable tool for researchers seeking to develop novel therapeutic agents and advanced materials. As ongoing research continues to uncover new applications for this compound, its significance is poised to grow even further, solidifying its place as a cornerstone of modern chemical synthesis and drug discovery.

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