210345-56-5

Usage

Uses

Used in Organic Synthesis:
5-Bromoindole-2-carboxylic acid methyl ester is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-Bromoindole-2-carboxylic acid methyl ester is utilized as a precursor in the development of pharmaceuticals. Its unique properties allow for the construction of potential drug candidates with specific therapeutic targets.
Used in Pharmaceutical Production:
5-Bromoindole-2-carboxylic acid methyl ester is employed as a key ingredient in the manufacturing process of certain pharmaceuticals. Its incorporation aids in the development of drugs with desired pharmacological properties.
Used in Agrochemicals:
5-Bromoindole-2-carboxylic acid methyl ester also finds application in the agrochemical industry, where it is used as a building block for the synthesis of agrochemicals. Its role is crucial in creating compounds that can protect crops and enhance agricultural productivity.
Used in the Production of Fine Chemicals:
5-Bromoindole-2-carboxylic acid methyl ester is utilized in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including pharmaceuticals, fragrances, and flavors. Its versatility ensures the creation of specialty chemicals with specific applications.

InChI:InChI=1/C10H8BrNO2/c1-14-10(13)9-5-6-4-7(11)2-3-8(6)12-9/h2-5,12H,1H3

Upstream product

• 67-56-1 methanol 
• 7254-19-5 5-bromo-2-indolecarboxylic acid 
• 66416-72-6 4-bromo-2-iodoaniline 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 3132-99-8 m-bromobenzoic aldehyde 
• 1586740-56-8 (Z)-methyl 3-(2-aminophenyl)-2-bromoacrylate 
• 1402454-70-9 methyl (Z)-2-bromo-3-(2-nitrophenyl)propenoate 
• 1586740-68-2 (Z)-methyl 3-(2-amino-5-bromophenyl)-2-bromoacrylate 
• 552-89-6 2-nitro-benzaldehyde 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 956903-53-0 methyl 2-(4-bromophenylhydrazono)propionate 

Downstream Products

• 1179587-99-5 methyl 5-bromo-3-(3,4,5-trimethoxybenzoyl)-1H-indole-2-carboxylate 
• 20948-71-4 5-bromo-indole-2-carbohydrazide 
• 1609930-25-7 ethyl 5-bromo-3-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-1H-indol-2-ylcarbamate 

Relevant academic research and scientific papers

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Calcium-Catalyzed Formal [5 + 2] Cycloadditions of Alkylidene β-Ketoesters with Olefins: Chemodivergent Synthesis of Highly Functionalized Cyclohepta[ b]indole Derivatives

The calcium-catalyzed, formal [5 + 2] cycloaddition of indolyl alkylidene β-ketoesters with mono- A nd disubstituted aryl olefins to form cyclohepta[b]indole derivatives has been established. Unanticipated chemodivergence with phenyl vinyl sulfide/ether revealed a double [5 + 2] cycloaddition cascade providing ethano-bridged cyclohepta[b]indoles. Overall, the method's highlights include: (1) use of a green, calcium-based catalyst (2.5 mol % loading); (2) reaction times under 1 h; (3) mild reaction conditions; (4) substrate-derived chemodivergence; (5) functional group tolerance; and (6) examples of derivatization.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate

An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee) and chemoselectivity (3/4>19:1 in most cases).

BACTERIAL EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula I and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.

INDOLE DERIVATIVES AS EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula (I): and salts thereof. Also disclosed are compositions comprising compounds of formula I and compounds of formula I for use in treating or preventing bacterial infections.

Design, Synthesis, and Evaluation of Novel Auxin Mimic Herbicides

Due to the key roles of auxins as master regulators of plant growth, there is considerable interest in the development of compounds with auxin-like properties for growth management and weed control applications. Herein, we describe the design and multiste

Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis

The enantioselective borylative dearomatization of a heteroaromatic compound has been achieved using a copper(I) catalyst and a diboron reagent. This reaction involves the regio- and enantioselective addition of active borylcopper(I) species to indole-2-carboxylates, followed by the diastereoselective protonation of the resulting copper(I) enolate to give the corresponding chiral indolines, which bear consecutive stereogenic centers.

CuI-catalyzed intramolecular cyclization of 3-(2-aminophenyl)-2- bromoacrylate: Synthesis of 2-carboxyindoles

A new approach was described for the synthesis of substituted 2-carboxyindole using 3-(2-aminophenyl)-2-bromo-acrylates through a CuI-catalyzed intramolecular coupling. The reactions were mild, rapid and with good to excellent yields.

Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile

A novel series of trifluoromethyl indole derivatives have been designed, synthesized and evaluated for anti-HIV-1 activities in MT-2 cells. The hydrophobic constant, acute toxicity, carcinogenicity and mutagenicity were predicted. Trifluoromethyl indoles 10i and 10k showed extremely promising activities against WT HIV-1 with IC50 values at the low nanomolar level, similar to efavirenz, better than nevirapine, and also possessed higher potency towards the drug-resistant mutant strain Y181C than nevirapine. Preliminary SAR and docking studies of detailed binding mode provided some insights for discovery of more potent NNRTIs. the Partner Organisations 2014.