56366-26-8

Upstream product

• 1006-94-6 5-methoxylindole 
• 108-86-1 bromobenzene 
• 1190709-19-3 5-methoxy-3-phenyl-1-(phenylsulfonyl)-1H-indole 
• 1516-21-8 4-methoxynitrosobenzene 
• 536-74-3 phenylacetylene 
• 108-94-1 cyclohexanone 
• 591-50-4 iodobenzene 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 33863-75-1 (±)-trans-phenyloxiriane-2-carbonitrile 
• 60-12-8 2-phenylethanol 
• 122-78-1 phenylacetaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 880771-40-4 3-bromo-5-methoxy-1-(phenylsulfonyl)-1H-indole 
• 85092-83-7 3-bromo-5-methoxy-1H-indole 

Downstream Products

• 1263146-02-6 7-methoxy-1,3,3,9-tetraphenyl-3H-pyrrolo[1,2-a]indole 
• 1458680-40-4 ethyl 2,2-difluoro-2-(5-methoxy-3-phenyl-1Hindol-2-yl)acetate 

Relevant academic research and scientific papers

Synthesis method of novel HuR inhibitor 1-benzenesulfonyl-3-phenylindole-4, 5-diketone

The invention discloses a synthesis method of a novel HuR inhibitor 1-benzenesulfonyl-3-phenylindole-4, 5-diketone, 5-methoxyindole is used as an initial raw material, C-3 site of 5-methoxyindole and aryl halide region are subjected to selective arylation, then benzenesulfonyl chloride is used for treatment to prepare 1-benzenesulfonyl-3-phenylindole, and finally, by carrying out demethylation and oxidation, a target product, namely the 1-benzenesulfonyl-3-phenylindole-4, 5-diketone is synthesized . The synthesis method has the advantages of simple synthesis route, short reaction time, simplicity in operation and the like.

Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands

The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).

Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group

A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 a

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons

3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb2O5/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic Nb2O5/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

Metal-free and regiospecific synthesis of 3-arylindoles

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri

A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water

The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines

An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C?H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.

Interfering with HuR-RNA Interaction: Design, Synthesis and Biological Characterization of Tanshinone Mimics as Novel, Effective HuR Inhibitors

The human antigen R (HuR) is an RNA-binding protein known to modulate the expression of target mRNA coding for proteins involved in inflammation, tumorigenesis, and stress responses and is a valuable drug target. We previously found that dihydrotanshinone

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.