Some common heterocyclic compound, 117832-17-4, name is 2-Iodo-4,5-dimethylaniline, molecular formula is C8H10IN, 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. category: iodides-buliding-blocks
Preparation 2.65,6-Dimethyl-1 /-/-indole-3-carboxylic acid.(VIII): X = CH; R4 = Me; R5 = Me.Step 1 : 3-[(2-lodo-4,5-dimethylphenyl)amino]benzyl acrylate (XVIII).60.8 g of lithium chloride is added to a solution of 15.5 g of [1 ,4]- benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Then a solution of 35.1 g of 2-iodo-4,5- dimethylaniline (prepared according to J. Med. Chem 2001 , 44, 3856-3871 ) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-de (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1 H, d); 5.18 (2H, s); 7.23 (1 H, s); 7.30-7.45 (5H, m); 7.59 (1 H, s); 7.72 (1 H, dd); 10.05 (1 H, d).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 117832-17-4, its application will become more common.
Reference:
Patent; SANOFI; BADORC, Alain; BOLDRON, Christophe; DELESQUE, Nathalie; FOSSEY, Valerie; LASSALLE, Gilbert; YVON, Xavier; WO2012/146318; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com