28059-24-7

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE is used as a building block for the synthesis of various pharmaceutical drugs due to its versatile reactivity and unique structure, which contribute to the development of new therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE is used as a reagent for the synthesis of complex organic molecules, leveraging its unique properties to facilitate the creation of intricate chemical structures.
Used in Medicinal Chemistry Research:
METHYL 5,6-DIMETHOXY-1H-INDOLE-2-CARBOXYLATE is utilized in medicinal chemistry research for its wide range of biological activities, such as its anti-inflammatory, anti-bacterial, and antiviral properties, which make it a promising candidate for the development of new treatments and therapies.

InChI:InChI=1/C12H13NO4/c1-15-10-5-7-4-9(12(14)17-3)13-8(7)6-11(10)16-2/h4-6,13H,1-3H3

Upstream product

• 4305-32-2 5-hydroxy-6-methoxy-indole-2-carboxylic acid methyl ester 
• 74-88-4 methyl iodide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 20357-25-9 6-nitroveratraldehyde 
• 855162-94-6 C₁₂H₁₃NO₆ 
• 186581-53-3 diazomethane 
• 10131-14-3 methyl 5,6-dihydroxy-1H-indole-2-carboxylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 886854-07-5 2-(2,2-dibromovinyl)-4,5-dimethoxyphenylamine 
• 157670-07-0 2-azido-3-(3',4'-dimethoxyphenyl)acrylic acid methyl ester 
• 690639-23-7 methyl 2-azido-3-(3',4'-dimethoxyphenyl)-propenoate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 690639-24-8 5,6-dimethoxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 
• 690639-25-9 5,6-dihydroxy-1H-indole-2-carboxylic acid pentafluorophenyl ester 
• 14430-23-0 5,6-dimethoxyindole 
• 142769-27-5 5,6-dimethoxy-1H-indole-3-carbaldehyde 
• 812652-87-2 5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indole-3-carbaldehyde 
• 812653-12-6 16-[5,6-dimethoxy-1-(4-methoxybenzenesulfonyl)-1H-indol-3-yl]hexadecan-1-ol 
• 812653-13-7 18-[5,6-dimethoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-octadecan-1-ol 
• 157670-10-5 [2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-((S)-1-phenyl-ethyl)-amine 
• 157670-09-2 2-(5,6-Dimethoxy-1H-indol-3-yl)-2-oxo-N-((S)-1-phenyl-ethyl)-acetamide 
• 157670-11-6 (R)-6,7-Dimethoxy-1-methyl-2-((S)-1-phenyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline 

Relevant academic research and scientific papers

Role of solvent, pH, and molecular size in excited-state deactivation of key eumelanin building blocks: Implications for melanin pigment photostability

Ultrafast time-resolved fluorescence spectroscopy has been used to investigate the excited-state dynamics of the basic eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA), its acetylated, methylated, and carboxylic ester derivatives, and two oligomers, a dimer and a trimer in the O-acetylated forms. The results show that (1) excited-state decays are faster for the trimer relative to the monomer; (2) for parent DHICA, excited-state lifetimes are much shorter in aqueous acidic medium (380 ps) as compared to organic solvent (acetonitrile, 2.6 ns); and (3) variation of fluorescence spectra and excited-state dynamics can be understood as a result of excited-state intramolecular proton transfer (ESIPT). The dependence on the DHICA oligomer size of the excited-state deactivation and its ESIPT mechanism provides important insight into the photostability and the photoprotective function of eumelanin. Mechanistic analogies with the corresponding processes in DNA and other biomolecules are recognized.

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.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Synthesis of symmetrical and unsymmetrical diindolylmethanes via acid-catalysed electrophilic substitution reactions

A range of activated indole-2-carboxylate derivatives was prepared via the Hemetsberger indole synthesis. Vilsmeier formylation was explored to establish regioselectivity and to prepare a range of new indole carbaldehydes. The indole aldehydes were reduce

Ligand-free copper-catalyzed one-pot synthesis of indole-2-carboxylic esters

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu 2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles. A simple, efficient, and facile synthetic route to indole-2-carboxylic esters through copper-catalyzed one-pot cascade reactions of commercially available, inexpensive 2-bromobenzaldehyde and glycine ester hydrochloride without the use of any external ligand under mild conditions is reported. Copyright

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles.

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.

Iron(II) triflate as a catalyst for the synthesis of indoles by intramolecular C-H amination

A practical iron-catalyzed intramolecular C-H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.

Concise, efficient and practical assembly of bromo-5,6-dimethoxyindole building blocks

A concise, efficient and simple route to a series of bromoindole building blocks is described. The synthetic routes are highlighted by purification-free preparation of o-nitrocinnamate intermediates and clean, modified Cadogan indole syntheses. The scope of this indole synthesis has been explored and expanded through the use of a range of solvents and easily removable phosphine reagents.

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.