924627-44-1

Basic information

• Product Name: [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester
• Synonyms: [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester
• CAS NO: 924627-44-1
• Molecular Weight: 280.326
• Mol File: 924627-44-1.mol

Chemical Properties

• CAS DataBase Reference: [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester(924627-44-1)
• EPA Substance Registry System: [2-(2-aminophenyl)-1H-indol-3-yl]acetic acid methyl ester(924627-44-1)

Safety Data

• Hazardous Substances Data: 924627-44-1(Hazardous Substances Data)

Upstream product

• 275361-65-4 Methyl 2-(2-iodo-1H-indol-3-yl)acetate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 615-36-1 2-bromoaniline 
• 1912-35-2 methyl 2-(2-bromo-1H-indol-3-yl)acetate 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 87-51-4 indole-3-acetic acid 
• 771-51-7 indole-3-acetonitrile 
• 1234713-22-4 [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-3-yl]acetic acid methyl ester 
• 615-43-0 2-iodophenylamine 
• 156049-34-2 (E)-methyl 3-(2-isocyanophenyl)acrylate 
• 10113-39-0 N-formyl-2-iodoaniline 
• 924627-36-1 [2-(2-tert-butoxycarbonylaminophenyl)-1H-indol-3-yl]acetic acid methyl ester 

Downstream Products

• 142273-18-5 paullone 

Relevant articles and documents

New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity

A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.

Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides

(Figure Presented) We have developed a method for the synthesis of 2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the Suzuki-Miyaura reaction. The utility of this method is demonstrated in the rapid synthesis of a kinase inhibitor, paullone. The reaction can be extended to the synthesis of 2-hydride indole and 2-silylindole by using hydroboronate (or hydrosilane) and silylboronate, respectively. Under these copper-catalyzed conditions, a quinoxaline ring system can also be constructed by using 1,2-isocyanobenzene as a substrate.

New route to the 5,12-dihydro-7H-benzo[2,3]azepino[4,5-b]indol-6-one core via a tin-mediated indole synthesis

A new route to the paullone scaffold was designed. The key step consisted in a free radical indole formation from an o-alkenyl arylisonitrile followed by Stille coupling with N-Boc-o-iodoaniline. After deprotection and closure of the seven-membered ring by lactamisation, parent or cyano-substituted paullones were obtained in moderate to good yields. Georg Thieme Verlag Stuttgart.