Heck cross-coupling reaction of 3-iodoindazoles with methyl acrylate: a mild and flexible strategy to design 2-aza tryptamines

In order to design 2-aza bioisosteres of tryptamine, serotonin or melatonin, the conditions of the Heck coupling reaction of 3-iodoindazoles with methyl acrylate are studied. This reaction authorizes the synthesis of 3-indazolylpropenoates as key intermediates to prepare 3-indazolylpropionic acids and 3-indazolylethylamines. The flexible synthetic strategy allows molecular diversity.