46193-76-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
As a building block in organic synthesis, Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate is utilized for the production of a range of organic compounds. Its presence in the synthesis process can lead to the creation of novel materials with potential applications in various fields.
Used in Chemical Research:
In the field of chemical research, Ethyl 4H-thieno[2,3-d]pyrrole-5-carboxylate is employed as a starting material for the synthesis of new organic materials. Its reactivity and structural features make it a valuable asset for exploring new chemical reactions and developing innovative compounds.

InChI:InChI=1/C9H9NO2S/c1-2-12-9(11)7-5-8-6(10-7)3-4-13-8/h3-5,10H,2H2,1H3

Upstream product

• 35355-50-1 ethyl 2-azido-3-(thiophen-2-yl)acrylate 
• 1056976-66-9 ethyl (Z)-2-azido-3-(2-thienyl)prop-2-enoate 
• 64-17-5 ethanol 
• 39793-31-2 4H-thieno[3,2-b]pyrrole-5-carboxylic acid 
• 60859-84-9 ethyl (Z)-2-nitro-3-(thiophen-2-yl)acrylate 
• 98-03-3 thiophene-2-carbaldehyde 
• 637-81-0 ethyl-2-azidoacetate 
• 67268-40-0 N-acetyl-N-(2-formyl-thiophen-3-yl)-glycine ethyl ester 

Downstream Products

• 15811-13-9 ethyl 6-[(dimethylamino)methyl]-4H-thieno[3,2-b]pyrrole-5-carboxylate 
• 898552-84-6 2-(4-nitrophenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid ethyl ester 
• 238748-91-9 Ethyl 4-(3,4-dichlorobenzyl)thieno[3,2-b ]pyrrole-5-carboxylate 
• 878657-01-3 (4H-thieno[3,2-b]pyrrol-5-yl)methanol 
• 837390-55-3 4-benzyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid 
• 606102-24-3 ethyl 4-benzyl-4H-thieno[3,2-b]pyrrole-5-carboxylate 
• 1533402-16-2 C₂₇H₂₃NO₃S 
• 1533402-17-3 C₃₆H₄₁NS 
• 1533402-18-4 C₄₀H₃₀BF₂N₃O₄S₂ 
• 1533402-19-5 C₅₂H₅₄BF₂N₃S₂ 
• 1533402-20-8 C₅₄H₄₂BF₂N₃O₆S₂ 
• 1533402-21-9 C₇₂H₇₈BF₂N₃S₂ 
• 1533402-10-6 C₂₃H₂₁NO₄S 
• 1533402-11-7 C₂₉H₃₃NO₂S 

Relevant academic research and scientific papers

Di-tungsten bis-carbene complexes linked by condensed heteroaromatic spacers

The 2,7-dilithiated substrates of 3,6-dimethylthieno[3,2-b]thiophene, N,N′-dimethylpyrrolo[3,2-b]pyrrole and N-methylthieno[3,2-b]pyrrole were reacted with W(CO)6 to give, after subsequent alkylation with Et 3OBF4, the ditungsten biscarbene complexes [(CO) 5W{C(OEt)XXC(OEt)} W(CO)5] (XX = condensed heteroaromatic spacers). Sites of attack during the dilithiation of the condensed rings were studied and compared, and the yields of the desired ditungsten biscarbene complexes optimized by changing the reaction conditions according to the role of the heteroatoms in the rings. The crystallographic data of the three ditungsten biscarbene complexes are reported and their structural features compared. The methyl substituents on the condensed heteroaromatic rings play an important role in determining the molecular configurations.

Corrigendum to: Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles: Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles (European Journal of Organic Chemistry, (2017), 2017, 14, (1902-1910), 10.1002/ejoc.201700165)

In the original article, compound 1f, ethyl 2-nitro-3-(thiophen-2-yl)acrylate was incorrectly assigned as the E isomer on the base of a NOESY NMR experiment. Reinvestigation of this assignment using different parameters evidenced that compound 1f is the Z isomer. We apologize for the error. The stereochemistry of the other compounds reported in the table is correct. The amended version of Tableà, entry 5 is reported below: The Authors 3 Palladium catalyzed cyclization of substituted 2- and 3-(2-nitrovinyl)thiophenes to thienopyrroles: reaction scope and limitation (Figure presented.) Reaction conditions: 1 (0.5 mmol), [Pd(Phen)2][BF4]2 (0.01 mmol), CH3CN (15 mL), Et3N (400 μL, 2.9 mmol), 150 °C, PCO = 5 bar, 3 h. Molar ratio 1a/L7/Pd = 50:8:1. Isolated yield. The product was detected by GC-MS but it was not possible to isolate it in a pure form. We thank Dr. Ruslan I. Baichurin and Prof. Sergey V. Makarenko (Organic chemistry department of Herzen State Pedagogical University of Russia) for suggesting us to reinvestigate our assignment.

COMPOUND AND FILM AND PHOTOELECTRIC DIODE AND ORGANIC SENSOR AND ELECTRONIC DEVICE

Disclosed are a compound represented by Chemical Formula 1, a film, a photoelectric diode, an organic sensor, and an electronic device. In Chemical Formula 1, Ar1 and Ar2, Z, L1, L2, and R1 to R6

New tetracyclic compound

The invention relates to a new tetracyclic compound. The tetracyclic compound has a structure shown in the formula (III) and can be used as a bromine domain and additional terminal (BET) inhibitor. The invention further relates to synthesis and application of the compounds in disease treatment. More specifically, the invention relates to a fused heterocyclic derivative used as a BET inhibitor, a method for the preparation of these compounds, and a disease and symptom treatment method conductive to inhibition of one or more BET bromine domains.

Divergent synthesis of indole-2-carboxylic acid derivatives via ligand-free copper-catalyzed ullmann coupling reaction

— This article describes a ligand-free copper-catalyzed Ullmami coupling reaction for the preparation of divergent indole-2-carboxylic acid derivatives including esters, amides and anhydrides. Various compounds 3, which could be synthesized from aldehydes conveniently, were used as substrate to provide the corresponding indole-2-carboxylic acid derivatives in moderate to good vields.

The effect of single atom replacement on organic thin film transistors: Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole

Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.

Thieno[3,2-b]pyrrole-5-carboxamides as New Reversible Inhibitors of Histone Lysine Demethylase KDM1A/LSD1. Part 1: High-Throughput Screening and Preliminary Exploration

Lysine specific demethylase 1 KDM1A (LSD1) regulates histone methylation and it is increasingly recognized as a potential therapeutic target in oncology. We report on a high-throughput screening campaign performed on KDM1A/CoREST, using a time-resolved fluorescence resonance energy transfer (TR-FRET) technology, to identify reversible inhibitors. The screening led to 115 hits for which we determined biochemical IC50, thus identifying four chemical series. After data analysis, we have prioritized the chemical series of N-phenyl-4H-thieno[3, 2-b]pyrrole-5-carboxamide for which we obtained X-ray structures of the most potent hit (compound 19, IC50 = 2.9 μM) in complex with the enzyme. Initial expansion of this chemical class, both modifying core structure and decorating benzamide moiety, was directed toward the definition of the moieties responsible for the interaction with the enzyme. Preliminary optimization led to compound 90, which inhibited the enzyme with a submicromolar IC50 (0.162 μM), capable of inhibiting the target in cells.

Trisubstituted thieno[3,2-b]pyrrole 5-carboxamides as potent inhibitors of alphaviruses

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus and is transmitted to humans by Aedes mosquitoes. Despite the re-emergence of CHIKV as an epidemic threat, there is no approved effective antiviral treatment currently available for CHIKV. Herein, we report the synthesis and structure-activity relationship studies of a class of thieno[3,2-b]pyrroles and the discovery of a trisubstituted thieno[3,2-b]pyrrole 5-carboxamide 15c that exhibits potent inhibitory activity against in vitro CHIKV infection. Compound 15c displayed low micromolar activity (EC50 value of ca. 2 μM) and limited cytotoxic liability (CC50 > 100 μM) therefore furnishing a selectivity index of greater than 32. Notably, 15c not only controlled viral RNA production, but efficiently inhibited the expression of CHIKV nsP1, nsP3, capsid, and E2 proteins at a concentration as low as 2.5 μM. More importantly, 15c also demonstrated broad spectrum antiviral activity against other clinically important alphaviruses such as O'nyong-nyong virus and Sindbis virus.

β- Thiophene-Fused BF2-Azadipyrromethenes as Near-Infrared Dyes

A facile synthetic route to a new class of near-IR β-thiophene-fused BF2-azadipyrromethenes (aza-BDTPs) is presented. Sharp absorption and fluorescence emission bands at around 800 nm were observed for these highly photostable aza-BDTPs, with a

Development of non-symmetric thiophene-fused BODIPYs

A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (λabs=532-647 nm; λem=547-664 nm; Φf/su