Production Method 1

170147-29-2

850568-62-6

Reaction Conditions

1.1 Reagents: Triisopropyl borate Solvents: Tetrahydrofuran ;  rt; rt → 0 °C
1.2 Reagents: Lithium diisopropylamide Solvents: Ethylbenzene ,  Tetrahydrofuran ,  Heptane ;  1 h, 0 °C; 30 min, 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  10 min, rt

Reference

Ruthenium half-sandwich complexes as protein kinase inhibitors: derivatization of the pyridocarbazole pharmacophore ligand

Pagano, Nicholas; Maksimoska, Jasna; Bregman, Howard; Williams, Douglas S.; Webster, Richard D.; et al, Organic & Biomolecular Chemistry, 2007, 5(8), 1218-1227

[5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid Raw materials

• Tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate

[5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid Preparation Products

• [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid (850568-62-6)

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• 5. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives Indolecarboxylic acids

Introduction to [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic Acid (CAS No. 850568-62-6)

[5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and synthetic biology due to its versatile applications. This compound, identified by the CAS number 850568-62-6, features a complex structure that includes a boronic acid moiety, a benzyloxy group, and a tert-butoxycarbonyl (Boc) protecting group, all attached to an indole core. The unique combination of these functional groups makes it a valuable intermediate in the synthesis of various biologically active molecules.

The boronic acid component of [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid is particularly noteworthy for its role in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern organic synthesis. This reaction allows for the formation of carbon-carbon bonds between boronic acids and aryl or vinyl halides, providing a powerful tool for constructing complex molecular architectures. The presence of the benzyloxy group enhances the stability of the boronic acid and facilitates its handling in synthetic protocols.

The tert-butoxycarbonyl (Boc) protecting group is another critical feature of this compound. Boc groups are widely used in peptide synthesis and other applications where temporary protection of functional groups is necessary. The Boc group not only protects the amine functionality but also provides a bulky steric environment, which can influence the reactivity and selectivity of subsequent reactions. This makes [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid an excellent building block for the construction of more complex molecules.

The indole core is a well-known pharmacophore in medicinal chemistry, with numerous natural products and drug candidates featuring this structural motif. Indole derivatives have been shown to exhibit a wide range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The incorporation of [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid into synthetic schemes allows researchers to explore new derivatives with potential therapeutic applications.

Recent research has highlighted the utility of [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid in the development of novel drug candidates. For instance, studies have demonstrated its use in the synthesis of indole-based inhibitors targeting specific enzymes involved in cancer progression. The boronic acid moiety enables further functionalization through cross-coupling reactions, allowing for the introduction of additional pharmacophoric elements that can enhance binding affinity and selectivity.

In addition to its role in drug discovery, [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid has been utilized in materials science and catalysis. The ability to precisely modify molecular structures using this compound has led to the development of new catalysts with improved performance characteristics. Furthermore, its incorporation into polymer materials has resulted in novel materials with enhanced mechanical and chemical properties.

The synthesis of [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid involves multiple steps, each requiring careful optimization to ensure high yield and purity. The process typically begins with the preparation of an indole derivative followed by functionalization with benzyloxy and Boc groups. The final step involves the introduction of the boronic acid moiety through lithiation followed by reaction with trialkyl borates.

Advances in synthetic methodologies have enabled more efficient routes to [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid, reducing reaction times and improving overall yields. These improvements have been driven by the demand for more sustainable and cost-effective synthetic processes. Additionally, computational methods have been employed to predict optimal reaction conditions and minimize unwanted side products.

The applications of [5-(benzyloxy)-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl]boronic acid are expected to expand as new research emerges. Its versatility as a synthetic intermediate makes it a valuable tool for chemists working in academia and industry. As our understanding of biological systems continues to grow, compounds like this will play an increasingly important role in the development of new therapies and materials.

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