1914-19-8

Usage

Chemical class

1H-Indole, 2-butyl-3-methylbelongs to the indole class of organic compounds.

Molecular weight

194.3 g/mol

Structure

A derivative of indole with a butyl group at the 2-position and a methyl group at the 3-position.

Appearance

Pale yellow

Odor

Characteristic

Usage

Commonly used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Biological activities

Exhibits antimicrobial and anti-inflammatory properties and has been studied for its potential therapeutic applications.

Upstream product

• 109-65-9 1-bromo-butane 
• 83-34-1 3-Methylindole 

Relevant academic research and scientific papers

Regioselective direct C-H alkylation of NH indoles and pyrroles by a palladium/norbornene-cocatalyzed process

Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a palladium/norbornene-cocatalyzed regioselective alkylation at the C-H bond adjacent to the NH group. A primary alkyl halide is used as the electrophile and the reaction proceeds smoothly under mild conditions to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields. Georg Thieme Verlag Stuttgart · New York.

Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: Mechanism and applications

A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles was developed based on a norbornene-mediated regioselective cascade C-H activation. The detailed reaction mechanism was investigated by NMR spectroscopic analyses, characterization of the key intermediate, deuterium labeling experiments, and kinetic studies. The results indicate that a catalytic cycle operates, in which an N-norbornene type palladacycle is formed as the key intermediate. Oxidative addition of alkyl bromide to the Pd(II) center in this intermediate is the rate-determining step of the reaction. The synthetic utility of this indole 2-alkylation method was demonstrated by its application in natural product total synthesis. A new and general strategy to synthesize Aspidosperma alkaloids was established employing the indole 2-alkylation reaction as the key step, and two structurally different Aspidosperma alkaloids, aspidospermidine and goniomitine, were synthesized in concise routes.