50614-84-1

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 1H-indole-4-carboxylate is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure allows for the creation of complex organic compounds that can be used in the development of new drugs and medications.
Used in Organic Chemistry Research:
Ethyl 1H-indole-4-carboxylate is used as a research tool in organic chemistry, particularly in the synthesis and study of indole-based compounds. Its versatile structure makes it a valuable component in the exploration of new chemical reactions and pathways.
Used in Drug Discovery:
Ethyl 1H-indole-4-carboxylate is used as a key component in drug discovery, where its properties can be exploited to design and develop new therapeutic agents. Its presence in the synthesis of pharmaceuticals can lead to the creation of novel drugs with potential applications in various medical fields.

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

Upstream product

• 112447-71-9 4-ethoxycarbonyl-1-tri-isopropylsilylindole 
• 91873-14-2 5-amino-3-ethoxy-3,4-dihydroisocoumarin 
• 2124-55-2 1H-indole-4-carboxylic acid 
• 7664-93-9 sulfuric acid 
• 52488-36-5 4-bromo-1H-indole 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 120-72-9 indole 
• 71516-34-2 2-((E)-2-Dimethylamino-vinyl)-3-nitro-benzoic acid ethyl ester 
• 59382-60-4 ethyl 2-methyl-3-nitrobenzoate 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 31706-23-7 ethyl 2-bromo-3-nitrobenzoate 
• 91873-12-0 ethyl 3-nitro-2-(trimethylsilylethynyl)benzoate 
• 91873-13-1 3-ethoxy-5-nitro-3,4-dihydroisocoumarin 

Downstream Products

• 1093258-02-6 ethyl 1-methyl-1H-indole-4-carboxylate 
• 862297-60-7 4-[(tert-butyldiphenylsilyloxy)methyl]indole 
• 862297-61-8 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde 
• 862297-62-9 ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate 
• 862297-63-0 ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate 
• 862297-56-1 4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 98664-90-5 ethyl (6aRS,9SR,9aSR)-hexahydro-7,7-dimethylisoindolo[4,5,6-cd]indole-9-carboxylate 
• 1381993-11-8 1-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-1H-indole-4-carboxylic acid ethyl ester 
• 1381992-68-2 (S,S,S)-N,N'-(3,3'-(ethane-1,2-diylbis(oxy))bis(propane-3,1-diyl))bis(1-(5-((S)-1-((S)-3-methyl-2-((S)-2-(methylamino)-propanamido)butanoyl)pyrrolidin-2-yl)pyridin-3-yl)-1H-indole-4-carboxamide) 
• 1074-86-8 4-formyl indole 
• 90924-06-4 1-methyl-1H-indole-4-carboxylic acid 
• 887922-92-1 indole-4-isocyanate 
• 1074-85-7 (1H-indol-4-yl)methanol 

Relevant academic research and scientific papers

HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor

HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the putatively mutagenic aromatic-amine building block that resulted in a novel, aminomethylindole compound family. The most balanced physico-chemical and pharmacological profile was found in case of compound 55. Docking study revealed an intersubunit binding site to be the most probable for our compounds. 55 demonstrated favorable cognitive enhancing profile not only in scopolamine-induced amnesia (place recognition test in mice) but also in natural forgetting (novel object recognition test in rats). Compound 55 was, furthermore, active in a cognitive paradigm of high translational value, namely in the rat touch screen visual discrimination test. Therefore, 55 was selected as a lead compound for further optimization. Based on the obtained favorable results, the invented aminomethylindole cluster may provide a viable approach for cognitive enhancement through positive allosteric modulation of α7 nAChRs.

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step

The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.

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.

Palladium-Catalyzed Carbonylation of Haloindoles: No Need for Protecting Groups

(Equation presented) For the first time, palladium-catalyzed carbonylations of unprotected bromoindoles have been performed successfully with different N- and 0-nucleophiles. Various indole carboxylic acid derivatives are accessible in excellent yield. For example, aminocarbonylation of 4-, 5-, 6-, or 7-bromoindole with arylethylpiperazines provides a direct one-step synthesis for CNS active amphetamine derivatives.

The synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfones

The first synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfone precursors has been achieved. The required sulfones, 3,4,5,6- tetrahydro-1H-cyclohex[cd]benzothiophene-2,2-dioxide and 1,3,4,5,6,7- hexahydrocyclohept[cd]benzothiophene-2,2-dioxide, were prepared from α- tetralone and benzosuberone utilizing a ring closure proceeding through a sulfonium salt intermediate. The same strategy failed when frying to prepare the tricyclic sulfone of the indane series. Other contrasting reactivity was also noticed when comparing the ability and ease of formation of tricyclic ether compounds. These results indicate that the later ring system is considerably strained.

SYNTHESIS OF 4-ACYLINDOLES VIA 2-(2-PHENYLSULFINYLVINYL)PYRROLE.

4-Acylindoles are readily obtained by the cycloaddition of 1-triisopropylsilyl-trans-2-(2-phenylsulfinylvinyl)pyrolle with electron deficient acetylenes followed by N-desilylation of the cycloadducts with fluoride ion.

Condensed Heteroaromatic Ring Systems. VI. Synthesis of Indoles and Pyrrolopyridines from o-Nitroarylacetylenes

Catalytic hydrogenation of o-nitrophenylacetaldehyde diethyl acetal over palladium-carbon, followed by intramolecular cyclization of the resulting o-aminophenylacetaldehyde diethyl acetal with hydrochloric acid, gave indole.Similarly, 4-methylindole, ethyl 5-indolecarboxylate, and various pyrrolopyridines were synthesized from the corresponding o-nitroarylacetaldehyde derivatives.The preparation of the desired o-nitroarylacetaldehydes was accomplished by the condensation of o-halonitroaromatics with trimethylsilylacetylene in the presence of dichloro-bis(triphenylphosphine)palladium as a catalyst, followed by ethanolysis of the resulting o-(trimethylsilylethenyl)nitroaromatics.Keywords - o-halonitroaromatic; o-cyanohaloaromatic; trimethylsilylacetylene; palladium-catalyzed reaction; cyclization; indole; pyrrolopyridine

SYNTHESIS OF INDOLE AND RELATED COMPOUNDS FROM HALO-NITROAROMATICS

5,7-dimethyl-6-azaindole was synthesized by treatment of 3-amino-2,6-dimethyl-4-pyridineacetaldehyde diethyl acetal with hydrochloric acid in boiling ethanol.According to the similar manner, indole and ethyl 4-indolecarboxylate were obtained from the corresponding 2-aminophenylacetaldehyde derivatives in satisfactory yields.The starting materials were easily prepared by palladium-catalyzed cross-coupling reaction of o-halonitroaromatics with trimethylsilylacetylene followed by the reaction with sodium ethoxide and catalytic reduction of the o-nitro group.

A New Synthesis of 4-Substituted Indoles via Tricarbonylarenechromium(0) Complexes

Tricarbonyl-(η6-1-tri-isopropylsilylindole)chromium(0), lithiated selectively at C-4 by n-butyl-lithium-N,N,N',N'-tetramethylethylenediamine (TMEDA), can be substituted in good yield by a range of electrophiles; the method has been used to synthesise 4-prenylindole.