138043-75-1

Upstream product

• 213881-70-0 methyl 1-benzyl-3-phenyl-1H-2-indolecarboxylate 
• 67-56-1 methanol 
• 3095-95-2 diethylphosphonoacetic acid 
• 615-43-0 2-iodophenylamine 
• 100-52-7 benzaldehyde 
• 615-36-1 2-bromoaniline 
• 124-41-4 sodium methylate 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 6915-67-9 3-phenyl-1H-indole-2-carboxylic acid 
• 534595-85-2 3-iodo-indole-2-carboxylic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 31827-04-0 methyl 3-hydroxy-1H-indole-2-carboxylate 
• 213881-58-4 methyl 1-benzyl-3-hydroxy-1H-2-indolecarboxylate 
• 213881-57-3 methyl 3-(tert-butyldimethylsilyloxy)-1H-2-indolecarboxylate 

Downstream Products

• 6915-67-9 3-phenyl-1H-indole-2-carboxylic acid 
• 1173839-06-9 11-phenyl-10H-indolo[1,2-a]indol-10-one 

Relevant academic research and scientific papers

Immobilized α-diazophosphonoacetate as a versatile key precursor for palladium catalyzed indole synthesis on a polymer support

Rh(II)-catalyzed N-H insertion reaction of immobilized α-diazophosphonoacetate with 2-haloanilines followed by Horner-Emmons reaction gave immobilized enaminoesters, which were efficiently cyclized to indoles via intramolecular palladium catalyzed reactio

Synthesis and evaluation of 2-carboxy indole derivatives as potent and selective anti-leukemic agents

Despite the success achieved in the treatment of acute lymphoblastic leukemia (ALL), the search for new drugs featuring selectivity against leukemia cells and effectiveness to prevent relapsed ALL is still highly desirable. Here, we described the synthesi

Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates

The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.

Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

Versatile base-catalyzed route to polycyclic heteroaromatic compounds by intramolecular Aza-Michael addition

A catalytic new synthetic approach to 3,4-dihydropyrazino[1,2-α] indol-1(2H)-ones by intramolecular 1,4-addition of readily available α,β-unsaturated esters, is described. Here, the use of a range of organic as well as inorganic bases (5-10 mol-%) allowed

Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a Ki value of 0.07 nM. X-ray crystallography of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR.

Solid-phase synthesis of indolecarboxylates using palladium-catalyzed reactions

Polymer-supported, palladium-catalyzed cyclization reactions effectively synthesized indolecarboxylates. Palladium-catalyzed carbon - carbon bond-forming reactions of immobilized enaminoesters followed by transesterification yielded indole 2- or 3-carboxylates with various functional groups on the benzene ring. Indolecarboxylates were efficiently cyclized via an intramolecular palladium-catalyzed amination reaction of immobilized N-substituted dehydrohalophenylalanines, and immobilized N-acetyl-dehydroalanines were efficiently converted into indolecarboxylates via tandem Heck-amination reactions.

Synthesis and reactivity of substituted 3- ([(trifluoromethyl)sulfonyl]oxy) 1H-indole-2-carboxylate in palladium- catalyzed reactions

Palladium-catalysed Suzuki and Stille reactions of substituted 3- indolyltriflate afforded the corresponding 3-substituted indoles. By contrast, the Heck reaction of allyl alcohol with such triflates gave 2- allyloxy-3-oxoindole derivatives rather than th