5257-24-9

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 1151, 1988 DOI: 10.1080/00397918808060902

InChI:InChI=1/C10H9NO/c1-7-8-4-2-3-5-9(8)11-10(7)6-12/h2-6,11H,1H3

Upstream product

• 83-34-1 3-Methylindole 
• 1478-41-7 diethoxycarbonium fluoroborate 
• 164261-56-7 1-(Phenylsulfonyl)-3-methyl-2-(bromomethyl)indole 
• 75-27-4 bromodichloromethane 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 23876-45-1 (3-methyl-1H-indol-2-yl)(p-tolyl)methanol 

Relevant academic research and scientific papers

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.

A facile preparation of N-protected indolaldehydes using a modified Hass procedure

The preparation of a variety of N-protected indolaldehydes is reported via the reaction of N-protected bromomethylindoles with 2-nitropropane using NaH/DMF.

Synthesis and structural analysis of (e)-2-(2'-nitrovinyl)indoles from the corresponding 2-formylindole derivatives

Preparation of 2-formylindoles was carried out from the appropriate methylindole by oxidation with selenium dioxide and by Vilsmeier formylation. The 2-(2'-nitrovinyl)indoles have been obtained by condensation of 2-formylindoles with nitroalkanes in the presence of ammonium chloride in good yields. In this reaction, only the (E)-isomer of the 2-(2'-nitrovinyl)indoles was observed by 1H nmr and NOE experiments. Evidence for an extended conjugation through the double bond and the nitro group can be evaluate by the deshielding effect on the olefinic protons. Moreover, the non-Beer's law behaviour in the uv-visible spectra suggest the existence of some sort of complex for these compounds.

First electrophilic substitutions of 3-substituted indoles with diethoxycarbenium tetrafluoroborate: Functionalized indole derivatives

The indoles 2a-2c react with diethoxycarbenium tetrafluoroborate (1) to furnish the indolecarbaldehydes 3a-3d. In the thermodynamically controlled reaction of 3-methylindole (2a) with 1 the tris(indolyl)methane 4 and diskatole (5), are formed in addition. The limitations of these reactions are discussed and evidence is presented for a C-3-ipso-attack and a Wagner-Meerwein rearrangement, respectively, leading to the formation of 3b or 3d.