Application of 6828-35-9,Some common heterocyclic compound, 6828-35-9, name is 5-Chloro-2-iodoaniline, molecular formula is C6H5ClIN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
c) To a stirred solution of 1-(4-ethynylbenzyl)-3,5-dimethyl-1 H-pyrazol-4-yl-acetic acid tert.- butyl ester (4.4g) and 5-chloro-2-iodophenylamine (3.4 g) in tetrahydrofuran (100 ml) at room temperature is added diisopropylethylamine (5.8 ml). The reaction is degassed and put under argon. Copper(l)iodide (260 mg) and bis(triphenylphosphine)palladiumdichloride (475 mg) are added. After 18 h, the reaction mixture is absorbed onto Extrelut and purified by flash chromatography (7:3 isocratic – cyclohexane:ethyl acetate) to yield a solid (4.3g; HPLC retention time 1.66 min (Method J)). The solid (4.2 g) is dissolved in N-methyl-2-pyrrolidone (25 ml) and the solution degassed and put under argon. Potassium tert-butoxide (4.1 g) is added and the reaction is then heated to 50C. After 15 h, further potassium tert-butoxide (1.0 g) is added. After 15 h the reaction temperature is increased to 75C. After 3 h, the reaction mixture is allowed to cool to room temperature and a copious amount of water is added. The reaction mixture is extracted twice with ethyl acetate and the aqueous phase is acidified to pH 3 with 1 M aqueous hydrochloric acid. The resultant precipitate is filtered off and triturated with hot acetonitrile to yield (1-[4-(6-Chloro-1 H-indol-2-yl)-benzyl]-3,5-dimethyl- 1 H-pyrazol-4-yl)-acetic acid (2.0 g; [M+H] = 394; HPLC retention time 1.51 min (Method E)).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-2-iodoaniline, its application will become more common.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MARTYRES, Domnic; ANDERSKEWITZ, Ralf; HOENKE, Christoph; KRIEGL, Jan; OOST, Thorsten; RIST, Wolfgang; SEITHER, Peter; WO2012/130633; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com