108763-47-9

Usage

Uses

Used in Pharmaceutical Industry:
Methyl Benzofuran-5-carboxylate is used as an intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drug candidates with biological activity.
Used in Agrochemical Industry:
Methyl Benzofuran-5-carboxylate is used as an intermediate in the synthesis of agrochemicals, leveraging its potential to enhance the properties of these compounds for agricultural applications.
Used in Antioxidant and Anti-inflammatory Applications:
Methyl Benzofuran-5-carboxylate is used as a building block in the preparation of compounds with antioxidant and anti-inflammatory properties, making it valuable in the development of new therapeutic agents for various health conditions.

InChI:InChI=1/C10H8O3/c1-12-10(11)8-2-3-9-7(6-8)4-5-13-9/h2-6H,1H3

Upstream product

• 699-18-3 2-[(E)-2-nitroethenyl]furan 
• 292638-85-8 acrylic acid methyl ester 
• 588702-80-1 methyl 2,3-dihydro-1-benzofuran-5-carboxylate 
• 53596-60-4 methyl 3-allyl-4-hydroxybenzoate 
• 52745-92-3 methyl (E)-3-nitroacrylate 
• 219763-27-6 methyl 4-((2,2-dimethoxy)ethoxy)benzoate 
• 90843-31-5 1-(2,3-dihydrobenzofuran-5-yl)ethanone 
• 140-88-5 ethyl acrylate 
• 67-56-1 methanol 
• 56540-70-6 benzofuran-5-carbonyl chloride 
• 23145-07-5 5-bromobenzofuran 
• 15126-06-4 methyl 3-iodo-4-hydroxybenzoate 
• 37470-46-5 4-hydroxy-3-iodobenzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 

Downstream Products

• 501892-90-6 methyl 3-bromo-1-benzofuran-5-carboxylate 
• 90721-27-0 benzofuran-5-carboxylic acid 
• 588702-80-1 methyl 2,3-dihydro-1-benzofuran-5-carboxylate 
• 31823-05-9 5-hydroxymethylbenzo[b]furan 
• 56540-70-6 benzofuran-5-carbonyl chloride 

Relevant academic research and scientific papers

Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans

Treatment of benzofurans with bis(pinacolato)diboron and Cs2CO3 under nickel-NHC catalysis resulted in the insertion of a boron atom into the C2-O bond of benzofurans to afford the corresponding oxaborins. The scope of benzofuran substrates is wide, and the reactions proceeded without loss of functional groups such as fluoro, methoxy, and ester that are potentially reactive under nickel catalysis. The boron-inserted products proved to be useful building blocks and subsequently underwent a series of transformations, one of which led to the synthesis of fluorescent π-expanded oxaborins.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights

Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.

Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles

Replacing the naphthalene C-unit of the anti-tuberculosis drug bedaquiline with a range of bicyclic heterocycles of widely differing lipophilicity gave analogs with a 4.5-fold range in clogP values. The biological results for these compounds indicate on average a lower clogP limit of about 5.0 in this series for retention of potent inhibitory activity (MIC90s) against M.tb in culture. Some of the compounds also showed a significant reduction in inhibition of hERG channel potassium current compared with bedaquiline, but there was no common structural feature that distinguished these.

Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade

A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).

Imidazole-containing condensed tricyclic compound and application thereof

The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.

ANTIBACTERIAL COMPOUNDS AND USES THEREOF

The present invention relates to compounds of formula (I) including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes

A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.

Mizoroki-Heck reactions catalyzed by dichloro{bis[1- (dicyclohexylphosphanyl)piperidine]}palladium: Palladium nanoparticle formation promoted by (water-induced) ligand degradation

The palladium-based dichlorobis[1-(dicyclohexylphosphanyl)piperidine] complex - [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2] is readily prepared in quantitative yield from the reaction of [Pd(cod)(Cl)2] (cod=cycloocta-1,5-diene) with two equivalents of 1-(dicyclohexylphosphanyl) piperidine in toluene under N2 within only a few minutes at room temperature. This complex is a highly active Heck catalyst with excellent functional group tolerance, which reliably operates at low catalyst loadings. Various activated, non-activated, deactivated, functionalized, sterically hindered, and heterocyclic aryl bromides, which may contain nitro, chloro or trifluoromethane groups, nitriles, acetales, ketones, aldehydes, ethers, esters, lactones, amides, anilines, phenols, alcohols, carboxylic acids, and heterocyclic aryl bromides, such as pyridines and derivatives, as well as thiophenes and aryl bromides containing methylsulfanyl groups have been successfully coupled with various (also functionalized) alkenes in excellent yields and selectivities (the E-isomers are typically exclusively formed) at 140 °C in the presence of 0.05 mol % of the catalyst in DMF. Even though lower catalyst loadings could be used for many electronically activated, non-activated and some electronically deactivated aryl bromides without noticeable loss of activity, the great advantage of the reaction protocol presented here lies in its reliability and general applicability, which allows its direct adoption to other aryl bromides without the neccessity of its modification. Experimental observations indicated that palladium nanoparticles are the catalytically active form. Consequently, whereas comparable levels of activity were observed for dichloro-bis(aminophosphine) complexes of palladium, a dramatic drop in activity was found for their phosphine-based analogue [(P(C6H 11)3)2Pd(Cl)2]. Copyright

Cycloisomerization of aromatic homo and bis-homopropargylic alcohols via catalytic ru vinylidenes: Formation of benzofurans and isochromenes

Ru-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic alcohols effectively afford benzofurans and isochromenes. These processes proved to be chemo- and regioselective (5-, and 6-endo cyclizations) derived from key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair is crucial for the catalytic cycle.