101283-15-2

Upstream product

• 104-94-9 4-methoxy-aniline 
• 4209-24-9 p-methylphenacyl chloride 
• 25287-24-5 4-methoxy-N-(1-p-tolylethyliden)aniline 
• 100-66-3 methoxybenzene 
• 619-41-0 4-(bromoacetyl)toluene 
• 624-31-7 4-tolyl iodide 
• 875296-43-8 (E)-N-(4-methoxyphenyl)-1-4-methylphenylethan-1-imine 
• 766-97-2 4-n-methylphenylacetylene 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 117616-04-3 4-methoxy-2-trimethylsilylmethylbenzanilide 

Downstream Products

• 1269219-58-0 6-methoxy-2-(4-methylphenyl)-quinazolin-4(3H)-one 

Relevant academic research and scientific papers

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

Copper-Catalyzed Direct Arylation of Indoles and Related (Hetero)arenes: A Ligandless and Solvent-free Approach

A ligandless and solvent-free copper-catalyzed method for the regioselective C?H bond arylation of indoles and related heteroarenes is reported. The use of CuCl efficiently catalyzes the direct coupling of diverse heteroarenes with aryl iodides via chelation-assistance. This reaction could tolerate sensitive and structurally diverse functionalities, including halides, ethers, thioethers, amines, indolyl, pyrrolyl and carbazolyl groups. The directing group, 2-pyridinyl can be smoothly removed to generate C-2 arylated free-NH indoles, and the arylated indoles can further be functionalized into Tryptamine derivatives. Preliminary mechanistic study revealed a radical pathway for the arylation reaction. (Figure presented.).

PROCESSES FOR PREPARING INDOLES

Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.

Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

A new approach to the synthesis of 2-substituted indoles: Reaction of dimetallated ortho-trimethylsilylmethylanilides with esters

The reaction of 2-trimethylsilylmethylanilides and esters in basic medium provides a new general method for the synthesis of indoles. The advantages of this method are the mild reaction conditions (-10-0°C), the ready availability of the starting materials and the use of a non-nucleophilic base (lithium 2,2,6,6-tetramethylpiperidide) to promote cyclisation.