3978-16-3

Usage

Uses

Used in Organic Synthesis:
2-[(Dimethylamino)methyl]indole is used as a synthetic building block for the development of various organic compounds. Its unique structure, which includes a dimethylamino group attached to a methylene bridge on an indole ring, allows for a wide range of chemical reactions and modifications, making it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
In the Pharmaceutical Industry:
2-[(Dimethylamino)methyl]indole is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its incorporation into drug molecules can potentially enhance their biological activity, selectivity, and pharmacokinetic properties, leading to the development of more effective medications.
In the Agrochemical Industry:
2-[(Dimethylamino)methyl]indole is also utilized in the agrochemical sector, where it can be employed in the synthesis of novel pesticides, herbicides, and other crop protection agents. Its unique chemical properties may contribute to the development of more targeted and environmentally friendly agrochemicals.
In the Dye and Pigment Industry:
2-[(Dimethylamino)methyl]indole can be used as a starting material for the production of dyes and pigments, particularly those with specific color properties or applications in various industries, such as textiles, plastics, and printing inks.
In the Research and Development Sector:
Due to its unique chemical structure and reactivity, 2-[(Dimethylamino)methyl]indole is also valuable in academic and industrial research settings. It can be used as a model compound to study various chemical reactions, mechanisms, and the development of new synthetic methodologies.

InChI:InChI=1/C11H14N2/c1-13(2)8-10-7-9-5-3-4-6-11(9)12-10/h3-7,12H,8H2,1-2H3

Upstream product

• 889868-60-4 ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate 
• 109-89-7 diethylamine 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 41979-44-6 N,N-diethyl-1H-indole-2-carboxamide 
• 148564-88-9 2,2,2-trifluoro-N-(2-(3-hydroxyprop-1-ynyl)phenyl)acetamide 
• 201813-43-6 2,2,2-Trifluoro-N-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-acetamide 
• 615-43-0 2-iodophenylamine 
• 287477-27-4 2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline 

Relevant academic research and scientific papers

Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines

A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.

Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu

Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficie

Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols and amines

A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate

The palladium-catalyzed reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1- propargyl carbonate with piperazines in the presence of Pd(PPh3) 4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields are also obtained with other secondary amines.