Tag: M.W:200-300

Electric Literature of 89415-54-3 ,Some common heterocyclic compound, 89415-54-3, molecular formula is C6H8BrN3, 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.

A mixture of the 5-bromo-/V-methyl-3-nitro-2-pyridinamine (1.14 g, 4.21 mmol assumed). and ammonium chloride (1.103 g, 20.62 mmol) in EtOH^O (8.5 mL of a 1 :1 solution) was stirred as iron (1 .152 g, 20.62 mmol) was added. The mixture was heated to reflux for ~ 2 hours. The mixture was allowed to cool to room temperature then diluted with EtOH and filtered through Celite. The filtrate was concentrated to yield a black tar which was diluted with EtOH then concentrated three times. The residue was slurried in EtOH then filtered. The filtrate was concentrated to yield a black solid which was dissolved in pyridine (15.1 mL). N, N dimethylaminopyridine (0.060 g, 0.49 mmoL) was added followed bybenzenesulfonylchlonde (0.63 mL, 4.91 mmol). The resulting mixture was stirred for one hour under a nitrogen atmosphere. The mixture was then concentrated. The residue diluted with EtOAc, washed with water two times, then saturated NaHC03 followed by brine, dried(Na2S0 ) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes). Fractions containing the product were combined and concentrated to yield A/-[5-bromo-2-(methylamino)-3-pyridinyl]benzenesulfonamide (0.859 g, 2.51 mmol 60% over 3 steps) as a grey solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (br. s., 1 H) 7.94 (br. s., 1 H) 7.75 – 7.64 (m, 3 H) 7.62 – 7.55 (m, 2 H) 6.92 (d, J=2.3 Hz, 1 H) 6.25 (br. s., 1 H) 2.68 (d, J=4.5 Hz, 3 H) LCMS: m/z 344 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

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;,
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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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C8H7BrN2

A solution of 19 (200 mg, 0.952 mmol) and 27 (162.8 mg, 0.952 mmol) in acetonitrile was added Na2CO3 (201.6 mg, 1.904 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (38.8 mg, 0.0476 mmol) was added to the reaction. The reaction mass was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90 C. under sealed conditions overnight, then allowed to cool to RT and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 silica mesh. The compound was eluted at 2% methanol chloroform as off-white colour solid 28.

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, 1111637-94-5, 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
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Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 623942-84-7 ,Some common heterocyclic compound, 623942-84-7, molecular formula is C7H8BrNO2, 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.

To a mixture of (3-bromo-6-methoxypyridin-2-yl)methanol (1.9 g, 8.7 mmol) in dichloromethane (100 mL) was added N-bromosuccinimide (1.8 g, 10 mmol) and triphenylphosphine (2.6 g, 10 mmol) under an ice bath condition and nitrogen atmosphere. The reaction mixture was stirred at rt for 3 h and then concentrated in vacuo, the residue was purified by column chromatography on a silica gel eluted with PE/EA (v/v = 30/1) to give the title compound as light yellow liquid (1.4 g, 57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623942-84-7, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; WANG, Xiaojun; YANG, Xinye; WU, Junwen; XIONG, Shaohui; PAN, Shengqiang; CAO, Shengtian; ZHANG, Yingjun; (121 pag.)WO2018/24224; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206968-92-4 , The common heterocyclic compound, 1206968-92-4, name is (5-Bromo-3-fluoropyridin-2-yl)methanol, molecular formula is C6H5BrFNO, 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.

[00186] To a solution of 69 (90 mg, 0.44 mmol) in anhydrous CH2C12 (1 mL) was added sulfonyl chloride (0.2 mL) at rt under N2. The mixture was stirred at reflux for 3 h. The mixture was concentrated under reduced pressure to afford crude chloride q (HC1 salt, 100 mg, 100%) as a yellow solid, which was used for the next step directly without further purification. LC-MS tR = 0.796 mm in 5-95 AB_1 .5 mm chromatography (Welch Xtimate MK RP-18e 25-2mm), MS (ESI) m/z 223.6 [M+H].

The synthetic route of 1206968-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 823221-93-8, 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 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of Compound 40a (3.10 g, 11.90 mmol) and sodium thiomethoxide (918 mg, 13.09 mmol) in dioxane (30 mL) was stirred for 16 hr at 110 C. After completion of the reaction, the reaction mixture was poured into water (150 mL), and the resulting mixture was extracted with ethyl acetate (100 mL×2). The organic phases were combined, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give Compound 40b (2.91 g). 1H NMR (400MHz, CDCl3) delta8.66 (s, 1H), 7.43 (s, 1H), 2.57 (s, 3H).

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 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; CHEN, Bin; YAO, Yuanshan; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (69 pag.)EP3489235; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887115-56-2, 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, 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, 887115-56-2, blongs to pyridine-derivatives compound. name: 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine

Step 2 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (compound 4-3) Compound 4-2 (3.1 g, 14.6 mmol) and bis(pinacolato) borate (11.1 g, 43.8 mmol) were added into a 250 ml reaction flask, and DMF (150 ml) and potassium acetate (4.3 g, 43.8 mmol) was added. After the air of reaction system was replaced by argon for three times, Pd(dppf)Cl2 (0.55 g, 0.73 mmol) was added, and then the air was replaced with nitrogen for another three times. The reaction system was heated to 90 C., and stirred for 8 h. The reaction progress was monitored by LC-MS. After completion of the reaction, the reaction solution was filtered, the filter cake was washed with EA (30 ml*3), and the filtrate was concentrated under reduced pressure to remove DMF and give compound 4-3 (13.5 g) as brown solid which was used directly in next reaction. MS m/z (ESI): 260.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,887115-56-2, its application will become more common.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936011-17-5 , The common heterocyclic compound, 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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.

To the solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bidepharm, 25.0 g, 115.72 mmol) in methanol (500 mL) was added sulfuric acid (14.19 mL, 231.5 mmol). After being stirred at rt for 18 hrs, the mixture was concentrated and added to the mixture solvent of aq. Na2C03 (150 mL) and EA (150 mL). The mixture was separated, the organic layer was washed with brine (50 mL), dried over Na2S04 and concentrated to give compound 76a (28.0 g) as a yellow oil. MS: calc?d 262 (MH+), measured 262 (MH+).

The synthetic route of 936011-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (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. 821791-58-6, name is Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

The following compounds were prepared as previously described with the addition of a chlorination step. An example of such a chlorination is described below. A mixture of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 g, 4.64 mmol) and NCS (0.68 g, 5.10 mmol) in DMF (30 mL) was stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with 0.1 N HCl solution. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 1.10 g (95%) of 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester.

The synthetic route of 821791-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marlow, Allison L.; Wallace, Eli; Seo, Jeongbeob; Lyssikatos, Joseph P.; Yang, Hong Woon; Blake, James; US2005/256123; (2005); 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.62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, molecular weight is 201.0207, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrN2O

EXAMPLE 64-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1 ,2-tf[1 ,2,4]triazin-2- yl)methylamino)picolinamideA mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1 ,2-7[1 .2,4]triazin-4(3H)-one (102 mg, 0.4 mmol), 4-bromopicolinamide (105 mg, 0.52 mmol) and DIEA (200 mu, 1 .13 mmol) in n- butanol (2.2 mL) was reacted under microwave irradiation at 190C during 22 h. After cooled to room temperature, the mixture was concentrated in vacuum and was purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile- methanol as eluents [0.1 % v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%).LRMS (m/z): 375 (M+1 )+.1H NMR (400 MHz, DMSO) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 – 7.73 (m, 1 H), 7.48 – 7.58 (m, 1 H), 7.39 – 7.48 (m, 1 H), 7.23 – 7.40 (m, 2 H), 7.03 – 7.14 (m, 1 H), 6.93 – 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 – 6.53 (m, 1 H), 3.86 – 3.99 (m, 2 H), 2.08 (s, 3 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62150-46-3, 4-Bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem