197775-85-2

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl-5-chloro-2-[(ethoxycarbonyl)oxy]-1H-indole-1-carboxylate is used as an intermediate in the synthesis of 2-Cyclobutenyl-3-trifluoromethyl-5-chloro-1H-indole-1-carboxylic Acid Ethyl Ester. ethyl-5-chloro-2-[(ethoxycarbonyl)
oxy]-1H-indole-1-carboxylate is further utilized in the preparation of novel GSK-3β inhibitors, which are potential anticancer agents. The development of these inhibitors is crucial for targeting specific cellular pathways involved in cancer cell growth and proliferation, offering a promising avenue for cancer treatment and therapy.

Upstream product

• 17630-75-0 5-chloro-indolin-2-one 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 197776-07-1 5-chloro-1-ethoxycarbonyl-2-oxo-2,3-dihydroindole 
• 301700-21-0 5-chloro-2-phenoxycarbonyloxy-indole-1-carboxylic acid ethyl ester 
• 301700-20-9 2-benzyloxycarbonyloxy-5-chloro-indole-1-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

TRICYCLIC SPIRO DERIVATIVES AS CRTH2 MODULATORS

The present invention is related to the use of spiro derivatives of Formula (I) for the treatment and/or prevention of allergic diseases, inflammatory dermatoses and other diseases with an inflammatory component. Specifically, the present invention is rel

New routes to oxindole derivatives

A new, practical synthesis of the antirheumatic oxindole derivative, tenidap, has been elaborated. The new approach has initiated studies on the mechanism of the acylation reactions of oxindoles. Methods have been developed for the synthesis of 1-[alkoxy(or aryloxy)carbonyl]- and 1,3-di[alkoxy(or aryloxy)carbonyl]oxindoles starting from oxindoles. The route designed for tenidap has provided a facile access to several analogues, too. On another front, new reaction conditions are described, which turn Wenkert's synthesis of 3-alkyloxindoles (by Raney nickel induced alkylation of oxindoles with alcohols) into a highly efficient synthetic tool. The method has been extended to the synthesis of 3-alkyloxindoles from isatins and to the preparation of 3-(ω-hydroxyalkyl)oxindoles from oxindoles and isatins. Springer-Verlag 2004.

Synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles

Two protocols have been developed for the synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles starting from the corresponding N,O-diacyl derivatives obtained by treatment of 2-oxindoles with chloroformic acid esters and triethylamine. Th

New practical synthesis of tenidap

The development of a new, practical synthesis to tenidap is described. N,O-Dialkoxy(aryloxy)carbonylation of 5-chloro-2-oxo-2,3-dihydroindole, followed by removal of the O-alkoxy-(aryloxy)carbonyl group gave 1-[alkoxy(aryloxy)carbonyl]-5-chloro-2-oxo-2,3-dihydroindoles in good yields. The latter compounds were thenoylated in the 3-position. The role of DMAP in the acylation reaction is discussed. The structures of the thenoylated products and their enolate salts were investigated both in solution and solid phases. Ammonolysis of 5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3- dihydroindole afforded the corresponding 1-carbamoyl derivative (tenidap) in high yield. The corresponding 1-ethoxy- and 1-methoxycarbonyl derivatives could not be similarly transformed to tenidap; loss of the alkoxycarbonyl moiety occurred instead of carbamoylation.