Category: 588729-99-1

Reference of 588729-99-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In vessel 1, thionyl chloride (110.0 kg) was added into water (430 kg) at Ca. 0C. The mixture was stirred at Ca. 3 C for 7 h before copper(I) chloride (0.27 kg) was added at Ca. 3 C.In vessel 2, 5-bromo-2-chloropyridin-3-amine (28.2 kg, 136 Mol) was mixed with 35% aqueous hydrochloric acid solution (202 kg) at Ca. 5C. A solution of sodium nitrite (8.5-14.1 kg) in water (19.7-25.4 kg) was then added at Ca. -10 C.The solution in Vessel 2 was added to the solution in vessel 1 while maintaining the temperature at Ca. -7C. The reaction mixture was stirred for 2 h at Ca. -2C. The solid product wasisolated by filtration and dried in vacuo at Ca. 23 C for 18 h. 30.9 kg of the title Compound was obtained in 66 %th yield and 84.3 % assay.

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H4BrClN2

5-Bromo-2-chloro-3-pyridinamine (10 g) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.5 ml) was added and stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at RT for 5 h. Further methanesulfonyl chloride (2.1 ml) was added and the mixture stired at RT overnight. The ph was adjusted to -6 by addition of 2M HCI (aq). The mixture was extracted with DCM (2 x 150 ml) and the combined organic layers were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M NaOH (50 ml) was added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and washed with DCM (150 ml). The aqueous layer was acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid, 13.45 g.LCMS (method B); Rt = 0.81 min, MH” = 285.

The synthetic route of 588729-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. HPLC of Formula: C5H4BrClN2

General procedure: To a solution of 1 (2.57mmol) in 8mL pyridine at 0C was added the pyridine solution of 4- fluoro sulfonyl chloride (4g, 19.4mmol) in drops and DMAP (20mg) to start the reaction. The mixture was warmed slowly to room temperature and stirred overnight. After the completion of the reaction (monitored by TLC), the reaction was quenched with water (30mL) and filtered. The filter cake was washed with water and EtOH to obtain white solid which was dissolved in MeOH (10mL) and added with 3mL saturated potassium carbonate solution. The mixture was stirred at room temperature for 6h and monitored by TLC. The reaction was quenched with water and extracted with EtOAc. The organic layer was collected and washed with water for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford white solid.

With the rapid development of chemical substances, we look forward to future research findings about 588729-99-1.

Reference:
Article; Yan, Guoyi; Pu, Chunlan; Lan, Suke; Zhong, Xinxin; Zhou, Meng; Hou, Xueyan; Yang, Jie; Shan, Huifang; Zhao, Lifeng; Li, Rui; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 667 – 686;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem