Category: 588729-99-1

Synthetic Route of 588729-99-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. A new synthetic method of this compound is introduced below.

Intermediate 50 N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 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 the addition of 2M HCI (aq). The mixture was then 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 hour 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 then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give title compound (13.45 g) as an off white solid. LCMS (Method B) R1 = 0.81 min, MH” = 285.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,588729-99-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147187; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., Product Details of 588729-99-1

Step 1. 6-Bromo-thiazolo [5,4-b] pyridin-2-yl amine:(Intermediatel) In a 50ml RB flask, 5-bromo-2-chloropyridin-3-amine (3.11 g, 15 mmol) was taken in cone. HCl (30 mL) and sonicated well to give pale brown solution. To this potassium thiocyanate (2.187 g, 22.50 mmol) was added and the resulting mixture was heated at 1000C for 6hrs .The reaction mixture was changed to pale yellow suspension after 30 minutes of reflux. The reaction mixture was evaporated in vacuo; ice-cold water was added to the residue, sonicated well and neutralized with saturated sodium carbonate under cooling condition. The precipitated solid was sonicated well, filtered and dried under high vacuum afforded the product as off-white solid (2.5gm)MS (ES+): 231 Rw C6H4BrN3S1H NMR 5(DMSO-dfi): 5.85 (bs, 2H,NH2); 7.3 (s, lH,Aro); 7.65 (s, lH,Aro).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application 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.

c) N-(5 -bromo-2-chloro-3 -pyridinyl)benzenesulfonamide. To a stirred solution of 3-amino-5-bromo-2-chloropyridine (24 mmol) in dichloromethane (50 mL) was added pyridine (37 mmol) followed by benzenesulfonyl chloride (35 mmol) drop wise over 5 min. The reaction mixture was stirred at room temperature for 18 h and evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel (15% hexanes/dichloromethane then 0-5% ethyl acetate in 15% hexanes/dichloromethane). During evaporation of the solvents the product precipitated. The resultant slurry was diluted with hexanes, filtered, and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. MS (ES) m/e 346.7 (M + H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39140; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1 ,Some common heterocyclic compound, 588729-99-1, molecular formula is C5H4BrClN2, its 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.

Example 163; N-(6-(6-Chloro-5-(4-methoxyphenyIsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide; Step 1. N-(5-Bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide; A solution of 4-methoxybenzenesulfonyl chloride (1 g, 5 mmol) and 3-amino-5-bromo-2-chloropyridine (0.45 g, 2 mmol) in 15 mL of pyridine was heated in a microwave vial at 100 C for 20 minutes. The mixture was then concentrated in vacuo and the residue was purified by a silica gel column chromatography to give first the di-sulfonamide compound (0.5 g, 42% yield): 1H NMR (300 MHz, chloroform -d) delta ppm 3.92 (s, 6 H) 6.94 – 7.09 (m, 4 H) 7.59 (d, J=2.34 Hz, 1 H) 7.81 – 7.98 (m, 4 H) 8.50 (d, J=2.34 Hz, 1 H); and then the mono-sulfonamide compound N-(5-bromo-2-chloropyridin-3-yl)-4- methoxybenzenesulfonamide (0.4 g, 49% yield): 1H NMR (300 MHz, chloroform -d) delta ppm 3.86 (s, 3 H) 6.84 – 7.06 (m, 3 H) 7.68 – 7.83 (m, 2 H) 8.08 – 8.21 (m, 2 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 588729-99-1, 3-Amino-5-bromo-2-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 588729-99-1.

a) (5-Bromo-2-chloro-pyridin-3-yl)-methyl-amine A solution of 5-bromo-2-chloro-pyridin-3-ylamine (CAS registry 588729-99-1) (565 mg, 2.72 mmol) in THF (4 ml) at 0 C. was treated with BuLi 1.6M in hexane (0.17 ml, 0.17 mmol), the resulting mixture was stirred at 0 C. for 0.5 h, then methyl iodide (0.17 ml, 2.72 mmol) was slowly added. The reaction mixture was allowed to warm to rt and was stirred for 18 h. The orange/brown mixture was poured into sat. aq. NaHCO3 soln., and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and purified by flash chromatography on silica gel (cyclohexane/EtOAc 95:5 to 60:40) to afford the title compound as an orange solid (354 mg, 59% yield). HPLC RtM1=0.94 min; ESIMS: 221, 223, 225 [(M+H)+]. 1H NMR (400 MHz, DMSO-d6): delta 7.65 (d, 1H), 7.14 (d, 1H), 6.11 (d, 1H), 2.74 (d, 3H).

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; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 588729-99-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, molecular weight is 207.4557, as common compound, the synthetic route is as follows.

(1) 5-bromo-3-amino-2-chloropyridine (0.10 g, 0.48 mmol),Pyridine (0.057g, 0.72mmol) was dissolved in dichloromethane (0.77mL) to prepare reaction solution 1, and phenylsulfonyl chloride (0.10g, 0.58mmol) was used to prepare reaction solution 2. The flow rate (0.4mL / min) set by the intelligent numerical control sampler was simultaneously introduced into the first three-way mixer (ambient temperature 0 C) through a 500 mum inner diameter picker tube and mixed, and then flowed out under its own pressure and entered In a temperature-controlled (25 C) picker tube with an inner diameter of 500 mum, the sulfonamidation reaction is completed under the condition of a set residence time t1 (1min), and then the post-pressure valve is used to obtain a first effluent;

The chemical industry reduces the impact on the environment during synthesis 588729-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fudan University; Zhuhai Fudan Chuangxin Institute; Ling Yun; Zhou Yaming; Jia Yu; Deng Mingli; Liu Xiaofeng; Yang Yongtai; Chen Zhenxia; (30 pag.)CN110498798; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588729-99-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Thionyl chloride (60.1 mL, 823 mmol) was added dropwise over 60 min to water (361 mL), cooled to 0 C, maintaining the temperature of the mixture 0-7 C. The solution was allowed to warm to 18 C over 17 h. copper(l) chloride (218 mg, 2.2 mmol) was added to the mixture, and the resultant yellow-green solution was cooled to -3 C using an acetone/ ice bath. 2) HCI (195 mL, 6.418 mol)(37% w/w) was added, with agitation, to 5-bromo-2-chloro-3- pyridineamine (25 g, 121 mmol), maintaining the temperature of the mixture below 30 C with ice cooling. The reaction mixture was cooled to -5 C using an ice/acetone bath and a solution of sodium nitrite (14.72 g, 213 mmol) in water (58 mL) was added dropwise over 45 min, maintaining the temperature of the reaction mixture between -5 to 0 C, the resultant slurry was cooled to -2 C and stirred for 10 min.3) The slurry from step (2) was cooled to -5 C and added to the solution obtained from step 1 ) over 30 min, maintaining the temperature of the reaction mixture between -3 to 0 C ( the slurry from step b was maintained at -5 C throughout the addition). As the reaction proceeded, a solid began to precipitate. When the addition was complete, the reaction mixture was agitated at 0 C for 75 min. The suspended solid was collected by vacuum filtration, washed with water, and dried under vacuum to give 5- bromo-2-chloro- 3-pyridinesulfonyl chloride. ES-LCMS: m/z 271 .94, 269.97 (M-1 ).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna, Lindsey; BOTYANSZKI, Janos; DICKERSON, Scott, Howard; DUAN, Maosheng; LEIVERS, Martin, Robert; MCFADYEN, Robert, Blount; MOORE, Christopher, Brooks; REDMAN, Aniko, Maria; SHOTWELL, John, Bradford; TAI, Vincent, W.-F.; TALLANT, Matthew, David; XUE, Jianjun; WO2012/37108; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 588729-99-1.

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 5-Bromo-2-chloro-3-pyridinamine [commercially available] (10 g, 48.2 mmol) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.46 ml, 96 mmol) added, and the mixture stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at room temperature for 5 h. A further portion of methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at room temperature overnight. The pH was adjusted to ?pH6 by the addition of 2M hydrochloric acid. The mixture was then extracted with dichloromethane (2*150 ml) the combined organic layers were dried using a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M sodium hydroxide (50 ml) added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and extracted with dichloromethane (150 ml). The aqueous layer was then 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).

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; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 588729-99-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: The 2-chloro-3-amino-5-bromo pyridine (500 mg, 2 . 46mmol) was dissolved in THF (10 ml), added LiHMDS (7.4 ml, 7 . 4mmol), stirring for ten minutes, then adding 4-fluorobenzenesulfonyl chloride (1.44g, 7 . 4mmol), stir at room temperature overnight. By adding dichloromethane (20 ml) dilution, washed with saturated sodium bicarbonate, with dichloromethane (4×30 ml) extraction, combined organic phase, dried, concentrated, the residue column chromatography (petroleum ether: ethyl acetate = 20:1) shall be N-(5-bromo-2-chloro-pyridine-3-yl) – 4-fluorobenzene sulfonaide (770 mg, 87%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; Shanghai Huilun Life Sciences & Technology Co., Ltd.; Cheng, Jianjun; Qin, Jihong; (61 pag.)CN103936762; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 588729-99-1, 3-Amino-5-bromo-2-chloropyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C5H4BrClN2, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrClN2

EXAMPLE 32; N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)-2- fluorobenzenesulfonamide; (l)2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-3- amine.; (Some starting materials may be obtained from Aldrich, St. Louis, MO) To a 5 ml microwave tube was added 5-bromo-2-chloropyridin-3-amine (0.1 g, 0.5 mmol), bis(pinacolato)diboron (0.2 g, 0.7 mmol), potassium acetate (0.2 g, 2 mmol), 1,1′- bis(diphenylphosphino)ferrocene]dichloride palladium(ii) (0.03 g, 0.04 mmol), and dioxane (3 mL). The vial was sealed and placed in Biotage Initiator microwave (Biotage, Charlottesville,VA) for 20 min at 110 0C. LC/MS showed no sign of starting material. Dioxane was removed in vacuo. The residue was partitioned between EtOAc/water. The organic layer was washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 (12g) chromatography with hexanes_acetone=85%: 15% as the solvent system to afford the desired product as light yellow solid (75 mg). A peak at 38 min was collected. The solvent was concentrated to afford the desired product as light yellow solid (75 mg). MS (ESI pos. ion) m/z: calc’d for CHH16BCIN2O2: 254.1; found: 255.3 (M+l). 1H NMR (300 MHz, CHL0R0F0RM- d) delta ppm 1.35 (s, 12 H) 4.03 (br. s., 2 H) 7.40 (d, J=1.61 Hz, 1 H) 8.14 (d, J=1.61 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588729-99-1, 3-Amino-5-bromo-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem