10075-48-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-3-methylindole is used as a key building block for the synthesis of various pharmaceuticals and fine chemicals. Its unique molecular structure allows it to be incorporated into a wide range of drug molecules, contributing to the development of new therapeutic agents.
Used in Chemical Intermediates Production:
In the chemical industry, 5-Bromo-3-methylindole is utilized as a chemical intermediate for the production of dyes, pigments, and other organic compounds. Its ability to be easily modified and incorporated into complex molecules makes it a valuable component in the creation of a diverse array of chemical products.
Used in Research and Development:
5-Bromo-3-methylindole is also employed in research and development settings, where its unique properties and reactivity are explored for potential applications in the synthesis of novel compounds and materials. Its versatility and mild aromatic odor make it an attractive candidate for further investigation and development in various scientific fields.
Overall, 5-Bromo-3-methylindole is a crucial chemical compound in both the pharmaceutical and chemical industries, with its applications ranging from the synthesis of pharmaceuticals and fine chemicals to the production of chemical intermediates and its use in research and development. Its mild aromatic odor and unique molecular structure contribute to its importance and versatility in these fields.

InChI:InChI=1/C9H8BrN/c1-6-5-11-9-3-2-7(10)4-8(6)9/h2-5,11H,1H3

Upstream product

• 70070-22-3 5-bromo-3-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 589-21-9 (4-bromophenyl)hydrazine 
• 586-78-7 para-nitrophenyl bromide 
• 125914-22-9 2-(5-bromo-2-nitrophenyl)acetonitrile 
• 92557-51-2 5-Bromo-indole-3-carbinol 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 10075-50-0 5-bromo-1H-indole 
• 67-56-1 methanol 

Downstream Products

• 222306-39-0 5-bromo-1-ethyl-2-[(4-fluorophenyl)(hydroxy)methyl]-3-methyl-1H-indole 
• 222306-38-9 5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole 
• 851524-90-8 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 10075-49-7 N-methyl-3-methyl-5-bromoindole 
• 1609470-56-5 C₁₇H₁₄BrF₂NO₂S 
• 1640122-66-2 N-acetyl-3-(4-methoxyphenyl)-3-methyl-5-bromoindoline 
• 1640122-86-6 3-(N-acetyl-5-bromo-3-methylindolin-3-yl)-1-tosylindole 
• 100954-32-3 3-benzyl-6-bromo-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Palladium-catalyzed C-H ethoxycarbonyldifluoromethylation of electron-rich heteroarenes

The first Pd-catalyzed C-H ethoxycarbonyldifluoromethylation with BrCF2CO2Et has been developed. The use of a bidentate phosphine ligand (Xantphos) is critical for the reaction to occur. A variety of electron-rich heteroarenes, including indoles, furans, thiophenes, and pyrroles, can be ethoxycarbonyldifluoromethylated in moderate to excellent yields. The reactions take place at the C-H bonds adjacent to the heteroatoms with high regioselectivity. This method provides a new protocol for the introduction of difuoroalkyl groups into electron-rich heteroarenes.

Direct oxidative coupling of N-acetyl indoles and phenols for the synthesis of benzofuroindolines related to phalarine

Inspired by the biogenetic synthesis of benzofuro-indoline-containing natural products, we designed an oxidative coupling between phenol and N-acetyl indoles. This straightforward and direct radical process, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and FeCl 3 allowed the regioselective synthesis of benzofuro[3,2-b]indolines, whose structure is found in the natural product phalarine.

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides

A highly efficient N,N′-dioxide-NiII catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98 % yield with up to 91 % enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C-C cleavage of oxiranes is accomplished by using a highly efficient N,N′-dioxide-NiII catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents a straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93percent yield and 98percent ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.

Enantioselective 2-alkylation of 3-substituted indoles with dual chiral lewis acid/hydrogen-bond-mediated catalyst

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation. This new bifunctional chiral Lewis acid/hydrogenbond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α, β-unsaturated 2-acyl imidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo- [1, 2-a]indole is demonstrated.

Constructing Saturated Guanidinum Heterocycles by Cycloaddition of N-Amidinyliminium Ions with Indoles

We report that structurally complex guanidinium heterocycles can be prepared in one step by regio- and stereoselective [4 + 2]-cycloadditions of N-amidinyliminium ions with indoles or benzothiophene. In contrast to reactions of these heterodienes with alkenes, density functional theory (DFT) calculations show that these cycloadditions take place in a concerted asynchronous fashion. The [4 + 2]-cycloaddition of N-amidinyliminium ions (1,3-diaza-1,3-dienes) with indoles and benzothiophene are distinctive, as related [4 + 2]-cycloadditions of N-acyliminium ions (1-oxa-3-aza-1,3-dienes) are apparently unknown.

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

Discovery of Potent and Orally Bioavailable Small Molecule Antagonists of Toll-like Receptors 7/8/9 (TLR7/8/9)

The toll-like receptor (TLR) family is an evolutionarily conserved component of the innate immune system, responsible for the early detection of foreign or endogenous threat signals. In the context of autoimmunity, the unintended recognition of self-motifs as foreign promotes initiation or propagation of disease. Overactivation of TLR7 and TLR9 have been implicated as factors contributing to autoimmune disorders such as psoriasis, arthritis, and lupus. In our search for small molecule antagonists of TLR7/9, 7f was identified as possessing excellent on-target potency for human TLR7/9 as well as for TLR8, with selectivity against other representative TLR family members. Good pharmacokinetic properties and a relatively balanced potency against TLR7 and TLR9 in mouse systems (systems which lack functional TLR8) made this an excellent in vivo tool compound, and efficacy from oral dosing in preclinical models of autoimmune disease was demonstrated.

Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.