1210023-65-6Relevant articles and documents
Direct N-Alkylation and Kemp Elimination Reactions of 1-Sulfonyl-1H-Indazoles
Tang, Meng,Chu, Bingjie,Chang, Xiaowei
, p. 2109 - 2116 (2018/07/31)
The reactions of 1-sulfonyl-1H-indazoles under basic conditions are discussed, and the direct N-alkylation and Kemp elimination reactions of these compounds are reported. A series of 2-(p-tosylamino)benzonitriles and N-alkyl indazoles were prepared in good yields. Moreover, the 2-(p-tosylamino)benzonitriles could be transformed into a diverse range of important derivatives in a one-pot reaction. This method was successfully applied to the total syntheses of quindolinone and cryptolepinone; quindolinone was prepared in a one-pot reaction from 1-sulfonyl-1H-indazole.
Route design and development of a MET kinase inhibitor: A copper-catalyzed preparation of an N 1 - Methylindazole
Kallman, Neil J.,Liu, Chin,Yates, Matthew H.,Linder, Ryan J.,Ruble, J. Craig,Kogut, Eugene F.,Patterson, Lawrence E.,Laird, Dana L. T.,Hansen, Marvin M.
, p. 501 - 510 (2014/05/06)
The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.
