On July 25, 2003, Yamazaki, Kazuo; Nakamura, Yosuke; Kondo, Yoshinori published an article.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Solid-Phase Synthesis of Indolecarboxylates Using Palladium-Catalyzed Reactions. And the article contained the following:
Indolecarboxylates are prepared on solid support using palladium-catalyzed reactions as the key steps. Supported β-amino-α,β-unsaturated esters are prepared either by attachment of tert-Bu acetoacetate to a resin followed by condensation with 2-haloanilines or by condensation of acryloyl chloride with a resin followed by Wacker-type oxidation of 2-haloanilines with the resin-bound acrylate in the presence of palladium catalysts. Supported α-amino-α,β-unsaturated esters are prepared by coupling of diethylphosphonoacetic acid to a resin followed by diazo transfer, rhodium-catalyzed insertion of 2-haloanilines, and base-mediated olefination with aldehydes. Palladium-catalyzed cyclization reactions of the α- or β-amino-α,β-unsaturated esters followed by cleavage of the resin-bound esters with sodium methoxide yields indolecarboxylates in moderate yields and purities. Rhodium-catalyzed insertion reactions of aminophenyl ketones and aldehydes with α-diazophosphonate esters followed by base-mediated cyclocondensation and cleavage from the resin with sodium methoxide also yields indolecarboxylates in low to moderate yields and purities. Resin-bound β-(halophenyl)-α-aminoacrylates are prepared either by attachment of an aminoacrylate to a resin followed by Heck arylation with an aryl halide or by rhodium-catalyzed insertion of an amine into a resin-bound α-diazophosphonate followed by olefination with halobenzaldehydes. Palladium-catalyzed cyclization of the resin-bound β-(halophenyl)-α-aminoacrylates followed by resin cleavage yields indolecarboxylates in 43-98% yields. A shorter version of this synthesis is also employed; palladium-catalyzed Heck reaction of 1,2-dihaloarenes with resin-bound acetylaminoacrylic acid followed by resin cleavage yields indolecarboxylates directly in 31-99% yields. Formylbromoarenes and -heteroarenes and methoxycarbonylarenes and -heteroarenes such as Me 2-bromobenzoate undergo palladium-catalyzed coupling with resin-bound acetylaminoacrylic acid followed by cyclization to yield fused pyridines and pyridones such as Me 1,2-dihydro-1-oxo-3-isoquinolinecarboxylate in 52-62% yields. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate
The Article related to indolecarboxylate solid phase preparation, fused pyridine pyridone solid phase preparation, solid phase preparation indolecarboxylate palladium rhodium catalyzed cyclization reaction and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles