新产品编号:1487589

Chemical Name: 2,4-Bis(6-bromo-1H-indol-3-yl)thiazole
项目整合开发状态: Biological Testing
项目研究机构: Shanghai Institute of Organic Chemistry (Originator)
合成路线:By cyclization of 6-bromo-1H-indole-3-carbothioamide (V) with 6-bromo-3-(2-bromoacetyl)-1-tosyl-1H-indole (VIII) in refluxing ethanol,followed by elimina-tion of the tosyl protecting group with NaOH in refluxing methanol.The intermediates 6-bromo-1H-indole-3-carbothioamide (V) and 6-bromo-3-(2-bromoacetyl)-1-tosyl-1H-indole (VIII) have been obtained as follows:6-Bromo-1H-indole-3-carbothioamide (V): The reaction of 6-bromoindole (I) with POCl3 and DMF,followed by hydrolysis with NaOH in refluxing water gives 6-bomoindole-3-carbaldehyde (II),which is treated with propyl nitrite and diammonium phosphate in refluxing acetic acid to yield the nitrile (III).Finally,the reaction of (III) with thioacetamide and HCl in refluxing DMF affords the interme-diate carbothioamide (V).6-Bromo-3-(2-bromoacetyl)-1-tosyl-1H-indole (VIII): The protection of 6-bromoindole (I) with tosyl chloride and NaOH in toluene/water gives the 6-bromo-1-tosylindole (VI),which is acetylated with acetic anhydride and AlCl3 in dichloro-methane yielding the 3-acetyl derivative (VII).Finally,the bromination of (VII) with CuBr2 in refluxing ethyl acetate/chloroform affords the target 3-(bromoacetyl) derivative (VIII).