158905-35-2

Usage

Source

Derived from 3-methylindole, a naturally occurring compound in jasmine and other plants

Use

Intermediate in the synthesis of pharmaceuticals and agrochemicals, particularly indole-based drugs and insecticides

Other applications

Potential use in organic synthesis and material science due to unique structure and reactivity

Physical state

Pale yellow solid

Melting point

Approximately 58-60 °C

Synthetic routes

Can be obtained through various synthetic methods

Upstream product

• 148836-41-3 1-bromo-4-chloro-2-iodo-benzene 
• 107-11-9 1-amino-2-propene 
• 133145-48-9 2-(2,4-dichlorophenyl)-2-methyloxirane 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 703-82-2 6-chloro-1H-indole-3-carbaldehyde 
• 17422-33-2 6-chloroindole 
• 67-56-1 methanol 
• 441801-02-1 ethyl 6-chloro-3-methyl-1H-indole-2-carboxylate 
• 441801-03-2 6-chloro-3-methylindole-2-carboxylate 

Downstream Products

• 1640122-69-5 N-acetyl-3-(4-methoxyphenyl)-3-methyl-6-chloroindoline 
• 1640122-87-7 3-(N-acetyl-6-chloro-3-methylindolin-3-yl)-1-tosylindole 

Relevant academic research and scientific papers

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization

The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents a straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93percent yield and 98percent ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).

Bifunctional Iron Complexes Catalyzed Alkylation of Indoles

Cyclopentadienone iron carbonyl complexes have been applied in alkylation of indoles with various benzylic alcohols, aliphatic alcohols (butanol, ethanol, methanol and 2-methylpentanol) via the hydrogen autotransfer strategy in mild reaction conditions. Experimental works highlight the role of the bifunctional iron complexes and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended the scope of substrates in iron catalyzed C?C bond formation. (Figure presented.).

Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines: Via the copper-catalyzed aerobic oxygenated CC bond of indoles

Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.

Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

AROMATIC HETEROCYCLIC COMPOUNDS AND THEIR APPLICATION IN PHARMACEUTICALS

Provided herein are novel aromatic heterocyclic compounds or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, and their uses for treating Alzheimer's disease. Also provided herein are pharmaceutical compositions containing such compounds, and methods for using such compounds or pharmaceutical compositions thereof to treat Alzheimer's disease.