Reference of 1150566-27-0,Some common heterocyclic compound, 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.
[0418] Step 1. 6- [(5-Fluoro-2-hydroxy-benzyl)-methyl-amino] -imidazo [1 ,2-b]pyridazine-3- carboxylic acid ethyl ester (42B). To a mixture of 4-fluoro-2-methylaminomethyl-phenol (20L, 305.2 mg, 1.97 mmol) and 6-chloro-imidazo [1 ,2-b]pyridazine-3-carboxylic acid ethyl ester (42A, 230 mg, 1.02 mmol) in DMSO (5 mL) was added KF (180 mg, 3.01 mmol). The reaction mixture was stirred at 120 C for 18 hours under nitrogen. The solution was then cooled to ambient temperature, diluted with water (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were further washed with water (3 x 50 mL) and brine (50 mL), dried over Na2504 and concentrated. The residue was then purified by a silica gel column eluting with EtOAc/hexane (0-50%, 10 CV) to afford the desired product as a white solid (240 mg, 69%). LC-MS (ESI) m/z 345.2 (M+H) ?H NMR (500 MHz, chloroform-d) oe 8.61 (s, 1H),8.17 (s, 1H), 7.91 (d, J= 10.0 Hz, 1H), 7.00-6.86 (m, 4H), 4.78 (s, 2H), 4.47 (qd, J= 7.2, 0.5 Hz, 2H), 3.17 (s, 3H), 1.41 (td, J= 7.1, 0.5 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, its application will become more common.
Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
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