683229-62-1

Basic information

• Product Name: 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER
• Synonyms: 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER;5-Methoxyindole-2-boronic acid pinacol ester
• CAS NO: 683229-62-1
• Molecular Formula: C₁₅H₂₀BNO₃
• Molecular Weight: 273.138
• Mol File: 683229-62-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER(683229-62-1)
• EPA Substance Registry System: 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER(683229-62-1)

Safety Data

• Hazardous Substances Data: 683229-62-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its reactivity in cross-coupling reactions allows for the efficient construction of molecular frameworks with potential applications in material science and pharmaceuticals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER is utilized as a precursor for the synthesis of pharmaceutical agents. Its unique structural features and ability to form stable compounds make it a promising candidate for the development of new drugs with improved therapeutic properties.
Used in Drug Discovery Research:
5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER is employed as a starting material in drug discovery research, where it is used to explore the synthesis of novel biologically active compounds. Its versatility in forming diverse molecular structures contributes to the identification of potential drug candidates with specific therapeutic targets.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER is used as a building block for the development of innovative drugs. Its stability and reactivity in chemical reactions facilitate the synthesis of new drug molecules with improved efficacy, selectivity, and safety profiles.
Used in Academic Research:
In academic research, 5-METHOXY-1H-INDOLE-2-BORONIC ACID PINACOL ESTER serves as a valuable tool for studying the fundamental aspects of organic and medicinal chemistry. Its unique properties and reactivity provide insights into the mechanisms of cross-coupling reactions and the design of new synthetic strategies for the preparation of biologically relevant molecules.

Upstream product

• 1006-94-6 5-methoxylindole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 847237-13-2 2-(3-(trifluoromethyl)phenyl)-1H-indole 

Relevant articles and documents

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

INHIBITORS OF CAMKK2 AND USES OF SAME

The present disclosure provides compounds suitable for inhibiting CaMKK2. Also provided are compositions and methods of treating diseases associated with CaMKK2.

Iridium(I)-Catalyzed C?H Borylation in Air by Using Mechanochemistry

Mechanochemistry has been applied for the first time to an iridium(I)-catalyzed C?H borylation reaction. By using either none or just a catalytic amount of a liquid, the mechanochemical C?H borylation of a series of heteroaromatic compounds proceeded in air to afford the corresponding arylboronates in good-to-excellent yields. A one-pot mechanochemical C?H borylation/Suzuki–Miyaura cross-coupling sequence for the direct synthesis of 2-aryl indole derivatives is also described. The present study constitutes an important milestone towards the development of industrially attractive solvent-free C?H bond functionalization processes in air.

Catalytic borylation of o-xylene and heteroarenes via C-H activation

Iridium and rhodium complexes catalyze the borylation of xylene and different heteroarenes using pinacolborane via C-H activation. Various five-membered heterocycles such as thiophene, pyrrole, thionaphthene, and indole derivatives yield the borylated pro