Tag: M.W:200-300

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.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.COA of Formula: C5H5IN2

General procedure: Procedure A : Suzuki coupling To a solution of iodopyridine (1 eq) in dioxane (5 mL/mmol), the boronic acid (1.5 eq), and 1 M Na2C03 aqueous solution (3 eq) were added and the reaction mixture was degassed with argon for 20 min. Then Bis(triphenylphosphine)palladium(ll) dichloride (0.2 eq) was added and the reaction mixture was heated at 100C for 16h. After completion of reaction, the reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography to afford the Suzuki coupling product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88511-27-7, 4-Amino-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116986-08-4, 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.116986-08-4, name is Methyl 2-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

A mixture of 2,6-dihydroxybenzaldehyde (leq) and methyl 2-(bromomethyl)nicotinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (l.2eq) was added to this mixture and the reaction was stirred at room temperature for 4 hours. The solvent was then evaporated and the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 5:2 to obtain pure product as pale yellow powder with a yield of 58%. IR (Diamond, cm-1): 2956, 1713, 1618, 1637, 1571, 1459, 1435, 1396, 1370, 1287, 1238, 1 170, 1 141 ; 1H-NMR (400 MHz, DMSO-dfi): d 1 1.67 (s, 1H), 10.19 (s, 1 H), 8.75 (dd, .7= 4.8, 1.68 Hz, 1H), 8.25 (dd, J= 7.84, 1.68 Hz, 1 H), 7.55 (m, 2H), 6.66 (d, J = 8.2 Hz, 1 H), 6.53 (d, J = 8.4 Hz, 1H), 5.58 (s, 2H), 3.79(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 193.68, 166.15, 162.26, 161.44, 155.02, 151.73, 138.75, 138.31 , 126.02, 123.60, 1 10.66, 109.49, 103.51, 70.59, 52.50. MS (ESI) m/z found 288.09 (M+H)+, 310.07 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 100% pure.

The chemical industry reduces the impact on the environment during synthesis 116986-08-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52605-98-8, 5-Bromo-2,3-dimethoxypyridine, 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, Computed Properties of C7H8BrNO2, blongs to pyridine-derivatives compound. Computed Properties of C7H8BrNO2

Add 2,3-dimethoxy-5-bromopyridine (218mg, 1.0mmol) to 5mL N, N-dimethylformamide solution, add cuprous cyanide (179.2mg, 4.0mmol), protect with argon Then, the temperature was raised to 160 C, and the reaction was completed after 8 hours of reaction. Cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated to remove the solvent, and column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain the product 2,3- Dimethoxy-5-cyanopyridine (i.e. compound 16, 164.2 mg, 1.0 mmol), white solid, yield 50%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-98-8, 5-Bromo-2,3-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhiyuan Pharmaceutical (Qingyuan) Co., Ltd.; Wu Deyan; Xie Ying; Zhou Huifang; (24 pag.)CN110498784; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 50735-34-7, Adding some certain compound to certain chemical reactions, such as: 50735-34-7, name is Methyl 2-amino-5-bromopyridine-3-carboxylate,molecular formula is C7H7BrN2O2, 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 50735-34-7.

A mixture of methyl 2-amino-5-bromonicotinate (1 g, 4.33 mmol), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.319 g, 5.19 mmol), potassium acetate (1.274 g, 12.98 mmol) in dioxane (20 mL) was degassed (3 x) with vacuum/nitrogen.1,1′- Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.353 g, 0.433 mmol) was added, and the mixture was degassed (2 x) and filled with N2. The reaction mixture was immersed in an oil bath at 80 C and stirred ON. The mixture was diluted with ethyl acetate, and washed with water and brine. The organic layer was collected, and the aqueous layers were sequentially extracted with ethyl acetate (2 x). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. After purification by Biotage flash chromatography (40 g column; 0% – 100% ethyl acetate in hexane), the obtained product was triturated with ether to afford methyl 2- amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (0.6 g, 2.157 mmol, 49.8 % yield) as a light tan solid. (0645) MS ESI m/z 279.18 (M+H)

According to the analysis of related databases, 50735-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1020253-15-9, 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.1020253-15-9, name is 4-Bromo-2-chloro-5-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

Step 105.2: 4-Bromo-5-methoxy-1-methyl-1 H-pyridin-2-one A solution of 4-bromo-2-chloro-5-methoxypyridine (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120C for 16 h in a sealed tube. After cooling, acetonitrile and a saturated aqueous NaHC03 solution were added and the mixture was stirred at rt over week-end. DCM was added and extracted. The organic layer was dried (Na2S04), filtered and concentrated to give the title compound. tR: 0.57 min (LC-MS 2); ESI-MS: 218.0/220.0 [M+H]+ (LC-MS 2).

The chemical industry reduces the impact on the environment during synthesis 1020253-15-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); 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. 189281-66-1, name is Methyl 2,6-dichloro-5-fluoronicotinate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H4Cl2FNO2

A mixture of 2,6-dichloro-5-fluoro-nicotinic acid methyl ester (1.00 g 4.46 mmol), trimethylboroxin (0.620 mL, 4.40 mmol), tetrakis(triphenylphosphine)palladium (0.500 g, 0.433 mmol) and potassium carbonate (1.50 g, 12.0 mmol) is heated at 110 0C overnight. The mixture is cooled to room temperature, diluted with water, and extracted with EtOAc. The combined organic phase is washed with water followed by brine, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography using a gradient of 0-30% EtOAc/heptane to provide 0.410 g (45.1%) of 2-chloro-5-fluoro-6-methyl-nicotinic acid methyl ester as a solid.

The synthetic route of 189281-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GINN, John David; MARSHALL, Daniel Richard; PROKOPOWICZ, Anthony S.; SCHYLER, Sabine; SIBLEY, Robert; TURNER, Michael Robert; WU, Di; WU, Frank; WO2010/126851; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884495-39-0, 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. 884495-39-0, name is 5-Bromo-2-methoxypyridin-3-amine, molecular formula is C6H7BrN2O, 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.

(1) 5-Bromo-3-amino-2-methoxypyridine (0.097 g, 0.48 mmol), pyridine (0.057 g, 0.72 mmol), and dissolved in dichloromethane (0.77 mL) to prepare a reaction solution 1, phenylsulfonyl chloride (0.10g, 0.58mmol) to prepare reaction solution 2,The flow rate (0.5mL / 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 Set a temperature-controlled (25 C) picker tube with an inner diameter of 500 mum, complete the sulfonamidation reaction under the set residence time t1 (0.5min), and then pass the back pressure valve to obtain the first effluent;

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 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine.

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

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. 13959-02-9, name is 3-Bromoisonicotinic acid, the common compound, a new synthetic route is introduced below. Formula: C6H4BrNO2

Step 1 [0182] To a suspension of 3-bromoisonicotinic acid (1) (4.0 g) in tetrahydrofuran (40 ml) were added oxalyl dichloride (1.82 ml) and dimethylformamide (one drop) at 0 C. and the mixture was stirred for 1 hour. To the reaction solution was added 28% aqueous ammonia (40 ml) and stirred for 40 minutes. After addition of ethyl acetate to the mixture, the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to afford Compound (2) (3.38 g). [0183] 1H-NMR (DMSO-d6) delta: 7.44 (1H, d, J=4.5 Hz), 7.83 (1H, s), 8.08 (1H, s), 8.60 (1H, d, J=4.5 Hz), 8.79 (1H, s).

The synthetic route of 13959-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; Mitsuoka, Yasunori; Kooriyama, Yuuji; US2013/217705; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79456-34-1, 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.79456-34-1, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4BrF3N2, molecular weight is 241.01, as common compound, the synthetic route is as follows.

Example 143 Synthesis of 5-cyclopropyl-3-(trifluoromethyl)pyridin-2-amine. To a solution of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (2 g, 7.2 mmol) in dioxane/H2O (100 mL/10 mL) was added cyclopropylboronic acid (1.425 g, 16.6 mmol), Pd(OAc)2 (186 mg, 0.83 mmol), PCy3 (465 mg, 1.66 mmol) and K3PO4 (3.523 g, 16.6 mmol). The reaction mixture was stirred at 100 C. for 14 h under nitrogen. Then the mixture was concentrated in vacuo. Water (100 mL) was added and the mixture was extracted with EtOAc (100 mL*3). The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography (PE/EtOAc=10/1) to give the 5-cyclopropyl-3-(trifluoromethyl)pyridin-2-amine as a yellow solid (708 mg, yield: 48%). ESI-MS [M+H]+: 203.1.

Statistics shows that 79456-34-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.162102-79-6, name is Dimethyl 4-bromopyridine-2,6-dicarboxylate, molecular formula is C9H8BrNO4, molecular weight is 274.07, as common compound, the synthetic route is as follows.Recommanded Product: Dimethyl 4-bromopyridine-2,6-dicarboxylate

Under nitrogen protection, add 4-bromopyridine-2,6-dicarboxylic acid dimethyl ester Ia (1.0equiv) and IIa (2.0equiv) to a 50mL round bottom flask, and then add N, N-dimethylformamide to dissolve.Then, 10% catalytic amount of tetrabutylammonium bromide was added, and the reaction was performed under reflux for 12 hours, followed by post-treatment: 30 mL of water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then subjected to column chromatography. To white solid IIIa, yield 87%.Then under the protection of nitrogen, add IIIa and 2.2equivs L-phenylglycinol to the sealed tube,Stir overnight at 100 C without solvent (the reaction is complete by TLC),Direct column chromatography gave white solid IVa in 99% yield.Then add IVa to the Schlenk bottle and then add anhydrous dichloromethane.Add 2.2 equivs diethylamine sulfur trifluoride reagent dropwise at -20 C, stir the reaction overnight, add 10% ammonia water to quench the reaction, add dichloromethane and water to extract 3 times, and dry with anhydrous sodium sulfate Column chromatography gave S1 as a white solid with a yield of 67%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; East China Normal University; Zhou Jian; Wang Cai; Liao Kui; Zhou Feng; (23 pag.)CN110305122; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem