139155-50-3

Upstream product

• 120-72-9 indole 
• 122-04-3 4-nitro-benzoyl chloride 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 14922-36-2 4-nitrophenylglyoxylic acid 
• 619-72-7 4-nitrobenzonitrile 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 139155-51-4 ethyl 4-[3-(4-nitrobenzoyl)-1H-indol-1-yl]butyrate 
• 139155-52-5 4-[3-(4-nitrobenzoyl)-1H-indol-1-yl]butyric acid 
• 139176-76-4 4-[3-(4-aminobenzoyl)-1H-indol-1-yl]butyric acid 

Relevant academic research and scientific papers

3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction

Within we report a general one-pot high-yielding Friedel-Crafts acylation of indole using acid chlorides and diethylaluminum chloride in gram scale quantities. This general synthesis affords products that are easily isolated and require no complex purification procedures.

Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation

Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.

Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates

An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.

Decarboxylative/decarbonylative C3-acylation of indoles: Via photocatalysis: A simple and efficient route to 3-acylindoles

A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with α-oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.

Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with α-oxocarboxylic acids

An efficient Cu-catalyzed decarboxylative C3-acylation of free (N-H) indoles using α-oxocarboxylic acids as acylating agents has been developed. This method was compatible with a variety of functional groups and provided an attractive alternative access to 3-acylindoles in moderate to high yields.

Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (NH) indoles with α-oxocarboxylic acids

A convenient and general method for acylation of free (NH) indoles via palladium-catalyzed decarboxylative cross-coupling reaction was developed. This process provided a useful method for the preparation of diverse 3-acylindoles in high yields utilizing a reaction with readily accessible reactants under mild conditions.

Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles

An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)2/2,2′-bipyridine system and with d-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed.

Iron powder promoted regio-selective friedel-crafts acylation of indole under solvent-free conditions

A facile, efficient and environment-friendly protocol for the regioselective synthesis of 3-acyl indoles has been developed by one-pot catalytic Friedel-Crafts acylation of indole in presence of the iron powder as catalyst under solvent-free conditions at room temperature.

Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles

Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a - g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2

4-(Benzoylindolizinyl)butyric acids; novel nonsteroidal inhibitors of steroid 5α-reductase. III

A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yllbutyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.