16382-18-6

Usage

Uses

Used in Organic Synthesis:
ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of derivatives, making it a valuable building block in the development of new chemical entities.
Used in Pharmaceutical Research:
In the pharmaceutical industry, ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE is used as a starting material for the development of potential drug candidates. Its structural features enable the design of molecules with specific biological activities, targeting various therapeutic areas such as pain management, inflammation, and neurological disorders.
Used in Chemical Research:
ETHYL 5,6-DIMETHOXYINDOLE-2-CARBOXYLATE is also employed in academic and industrial research settings to study the properties and reactivity of indole-based compounds. Its unique substitution pattern provides insights into the influence of structural modifications on the chemical behavior of indoles, contributing to the broader understanding of organic chemistry.

InChI:InChI=1/C13H15NO4/c1-4-18-13(15)10-5-8-6-11(16-2)12(17-3)7-9(8)14-10/h5-7,14H,4H2,1-3H3

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 2999-46-4 Ethyl isocyanoacetate 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 1016-58-6 6-nitroveratryl alcohol 
• 53413-67-5 6-nitroveratrylbromide 
• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 623-33-6 glycine ethyl ester hydrochloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 911301-33-2 (E/Z)-ethyl 2-azido-3-(3,4-dimethoxyphenyl)acrylate 
• 1906-82-7 ethyl acetamidoacetate 
• 6315-89-5 3,4-dimethoxyaniline 
• 86323-64-0 N-(3,4-dimethoxyphenyl)glycine ethyl ester 

Downstream Products

• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 121282-80-2 3-Formyl-5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester 
• 808137-34-0 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester 
• 808137-31-7 5,6-dimethoxy-3-o-tolylsulfanyl-1H-indole-2-carboxylic acid ethyl ester 
• 1272970-96-3 C₂₀H₂₁NO₅ 
• 1380695-62-4 C₂₂H₂₃NO₅ 
• 1380695-61-3 C₂₁H₂₁NO₅ 
• 1380695-60-2 C₂₁H₂₃NO₄ 

Relevant academic research and scientific papers

From far west to east: Joining the molecular architecture of imidazole-like ligands in ho-1 complexes

HO-1 overexpression has been reported in several cases/types of human malignancies. Unfortunately, poor clinical outcomes are reported in most of these cases, and the inhibition of HO-1 is considered a valuable and proven anticancer approach. To identify

SYNTHESIS OF INDOLES FROM ACETOACETIC ESTERS

The present invention relates to a synthesizing method of indole using acetoacetic ester and, more specifically, to a synthesizing method of indole which induces reduction of a nitro group into an amine group and aromatic cyclization with a ketone group through hydrogenation using a metal catalyst in a 2-nitrobenzyl ketone compound, after synthesizing the 2-nitrobenzyl ketone compound through deacetylation using a manganese (III) / cobalt (II) catalyst in a 2-nitrobenzyl acetone compound obtained by adding an acetoacetic ester compound in a 2-nitrobenzyl bromide compound.COPYRIGHT KIPO 2016

Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations

One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is

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.

Synthesis and agonistic activity at the GPR35 of 5,6-dihydroxyindole-2- carboxylic acid analogues

5,6-Dihydroxyindole-2-carboxylic acid (DHICA), an intermediate of melanin synthesis and an eumelanin building block, was recently discovered to be a GPR35 agonist with moderate potency. Here, we report the synthesis and pharmacological characterization of a series of DHICA analogues against GPR35 using both label-free dynamic mass redistribution and Tango β-arrestin translocation assays. This led to identification of novel GPR35 agonists with improved potency and/or having biased agonism.

Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs

A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5-7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3- (chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3- dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5-7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.

A ligand-free, copper-catalyzed cascade sequence to indole-2-carboxylic esters

A variety of indole-2-carboxylic esters are accessible in yields up to 61% through a ligand-free, coppercatalyzed reaction of a series of commercially available 2-halo aryl aldehydes with benign glycine amidoesters, including the common reagent ethyl acetamidoacetate. This one-pot, three-reaction format allows ready entry to the desired heterocycles from starting substrates in the reactivity order of iodo > bromo ≥ chloro substituents. An assortment of functional groups is tolerated, adding to the generality of this methodology.

Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process

A straightforward synthesis of indole-2-carboxylic esters was developed through a ligand-free copper-catalysed condensation/coupling/deformylation cascade process from 2-halo aryl aldehydes or ketones with ethyl isocyanoacetate. The reactions proceeded we

Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones

A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m. Georg Thieme Verlag Stuttgart.