32996-16-0

Basic information

• Product Name: ETHYL INDOLE-5-CARBOXYLATE
• Synonyms: RARECHEM AL BI 0874;INDOLE-5-CARBOXYLIC ACID ETHYL ESTER;ETHYL INDOLE-5-CARBOXYLATE;5-CARBETHOXYINDOLE;1H-Indole-5-carboxylicacidethylester;INDOLE-5-CARBOXYLIC ACID ETHYL ESTER (I5CAEt);ethyl 1H-indole-5-carboxylate
• CAS NO: 32996-16-0
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: Indoles and derivatives;Heterocycle-Indole series
• Mol File: 32996-16-0.mol

Chemical Properties

• Melting Point: 96.5-97.5 °C
• Boiling Point: 342.357°C at 760 mmHg
• Flash Point: 160.852°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.09±0.30(Predicted)
• CAS DataBase Reference: ETHYL INDOLE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL INDOLE-5-CARBOXYLATE(32996-16-0)
• EPA Substance Registry System: ETHYL INDOLE-5-CARBOXYLATE(32996-16-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 32996-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl Indole-5-carboxylate is used as a reagent for the synthesis of pyrazole-based cathepsin S inhibitors. Cathepsin S is a lysosomal cysteine protease that plays a crucial role in the immune system and has been implicated in various diseases, including cancer and neurodegenerative disorders. By inhibiting cathepsin S, these pyrazole-based inhibitors can potentially be used as therapeutic agents for treating these conditions.

InChI:InChI=1/C11H11NO2/c1-2-14-11(13)9-3-4-10-8(7-9)5-6-12-10/h3-7,12H,2H2,1H3

Upstream product

• 936840-07-2 ethyl 4-amino-3-ethynylbenzoate 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 64-17-5 ethanol 
• 94-09-7 p-aminoethylbenzoate 
• 62875-84-7 3-iodobenzocaine 
• 1034269-62-9 ethyl 4-amino-3-[2-(trimethylsilyl)ethynyl]benzoate 
• 10075-50-0 5-bromo-1H-indole 
• 1609-47-8 diethyl dicarbonate 
• 153602-65-4 isobutyl 6-oxopyrano<4,3-b>pyrrole-1-carboxylate 
• 623-47-2 propynoic acid ethyl ester 
• 153602-63-2 pyrano<4,3-b>pyrrol-6(1H)-one 

Downstream Products

• 329185-67-3 1H-indole-5-(N-phenyl)carboxamide 
• 406192-82-3 1H-indole-5-carbohydrazide 
• 118757-13-4 ethyl 1-phenylsulfonylindole-5-carboxylate 
• 496946-82-8 1-benzoyl-1H-indole-5-carboxylic acid 
• 739365-22-1 1-acetyl-1H-indole-5-carboxylic acid 
• 1095885-49-6 C₁₈H₁₆N₂O₃ 
• 420783-73-9 1-(N,N-dimethylsulfamoyl)-2-trimethylsilyl-1H-indole-5-(N-phenyl)carboxamide 
• 329185-63-9 1-(N,N-dimethylsulfamoyl)-1H-indole-5-(N-phenyl)carboxamide 
• 186129-25-9 1-methyl-1H-indole-5-carboxylic acid 

Relevant articles and documents

Discovery and synthesis of 2-amino-1-methyl-1H-imidazol-4(5H)-ones as GPCR ligands; an approach to develop breast cancer drugs via GPCR associated PAR1 and PI3Kinase inhibition mechanism

Efforts were taken to synthesis and characterize 2-amino-1-methyl-1H-imidazole-4(5H)-one derivatives (4a-u) through a four-step reaction. The achieved compounds in remarkable yield have characterized through standard analytical techniques such as FTIR, LC

Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides

Selective C-H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters

An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.

Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols

Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.

INDOLE DERIVATIVES USEFUL AS PPAR ACTIVATORS

There is provided according to the invention novel compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof: (I) useful as PPAR activators.

Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones

(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.

An efficient procedure for the deprotection of N-pivaloylindoles, carbazoles and β-carbolines with LDA

Treatment of variously substituted indoles with 2 equivalents of LDA at 40-45 °C led to their fast and efficient deprotection. This method was also extended to N-pivaloylcarbazoles and β-carbolines.

A simple and facile carboxylation method and its application for synthesis of liquid crystals

Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF 3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.

Pyrrole-2,3-quinodimethane Analogues in the Synthesis of Indoles. Part 2. Synthesis and Diels-Alder Reactions of 1,6-Dihydropyranopyrrol-6(1H)-ones

The pyranopyrrol-6-ones 7-9, 12 and 13 are stable cyclic analogues of pyrrole-2,3-quinodimethane, and undergo Diels-Alder reaction with a range of alkynes to give, after loss of carbon dioxide, indoles.

Intermediates for indoles

Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.