Day: April 6, 2022

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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.Computed Properties of C7H6N2OS

The following 4-methyl-2-methylthiooxazolopyridinium tosylates are prepared by heating the corresponding 2-methylthiooxazolopyridines (M. Y. Chu-Moyer and R. Berger, J. Org. Chem. 60, 5721-5725 (1995)) with one equivalent of methyl tosylate at 100-110 C. for one hour.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Molecular Probes, Inc.; US6664047; (2003); B1;,
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

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 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

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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

To a stirred solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.8 g, 4.06 mmol) in propan-2-ol (20 mL) was added concentrated sulphuric acid (0.5 mL) at 0 C. and the reaction mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was dissolved in water, basified with saturated bicarbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (20% ethyl acetate/hexane) to provide isopropyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate as a white solid (0.3 g, 33% yield): MS (ES) m/z 239.1 (M+H).

The synthetic route of 920966-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; ANDERSON, David Randolph; HOCKERMAN, Susan Landis; BLINN, James Robert; JACOBSEN, Eric Jon; US2019/135807; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588720-29-0, 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. 588720-29-0, name is Imidazo[1,5-a]pyridine-7-carboxylic acid, molecular formula is C8H6N2O2, 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.

[1145] A flask is charged with imidazo[1,5-a]pyridine-7-carboxylic acid (4.3 g, 19.9 mmol), (3R)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride (3.6 g, 18.2 mmol), DIEA (19 ml, 109 mmol), and DMF (200 ml). The reaction mixture is cooled to 0 C. and HATU (6.9 g, 18.2 mmol) is added to it. The mixture is allowed to stir at rt for 3 h. The mixture is diluted with MeOH (20 ml) and DOWEX 50WX2-40 ion exchange resin (2 g) is added; the mixture is adjetated in a water bath (35-40 C.) for 20 min, is filtered, and the resin washed with 3 portions of MeOH. The product is liberated from the resin by treatment with a solution of 20% NH4OH/MeOH. The basic alcohol washes are concentrated in vacuo to give a brown oil, which is purified by silica gel chromatography (10% MeOH/79% CH2Cl2/1% NH3OH) to give a yellow solid. The resulting solid is dissolved in MeOH (2 ml) and a solution of d-tartaric acid (0.151 g, 1.0 mmol) in MeOH (3.0 ml) is added to it. The solvent is removed under vacuum to give a yellow solid (0.49 g, 1.0 mmol). HRMS (FAB) calcd for C15H18N4O+H 271.1559, found 271.1560.

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 588720-29-0, Imidazo[1,5-a]pyridine-7-carboxylic acid.

Reference:
Patent; Rogers, Bruce N.; Piotrowski, David W.; Walker, Daniel Patrick; Jacobsen, Eric Jon; Acker, Brad A.; Wishka, Donn G.; Groppi JR., Vincent E.; US2003/236264; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 868551-30-8 , The common heterocyclic compound, 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate, molecular formula is C8H8N2O4, 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 methyl 4-methyl-5-nitropyridine-2-carboxylate (3.5g, 17.8mmol), dimethylformamide dimethylacetal (DMF-DMA) (3.6ml, 1.5eq) in acetonitrile (35mL) was heated in a microwave at 140C for 20 min. The solvent was removed. The residue (5.1 g) was carried onto the next step without further purification.

The synthetic route of 868551-30-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 709652-82-4, 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.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.

To 2-amino-5-bromonicotinonitrile (0.785 g, 3.96 mmol), triethylamine (0.553 mL, 3.96 mmol) and 4-dimethylaminoyridine (20 mg, 0.164 mmol) in CH2CI2 (25 mL) was added di-fe f-butyl- dicarbonate (2.16 g, 9.91 mmol) and the resulting mixture stirred at room temperature for 18h. Evaporated to dryness in vacuo and triturated in heptane (25 mL) for 72h. The resulting precipitate was filtered and washed with heptane (10 mL) to give imidodicarbonic acid, 2-[5- bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , -dimethylethyl) ester as a beige solid (1.1 g, 70% yield). 1 H NMR (400 Mhz, CDCI3, 298K) 1.51 (s, 18H) 8.16 (d, 1 H) 8.77 (d, 1 H). LCMS: [M+H]+=398/400.1 , Rt (4)= 1.43 min.

The chemical industry reduces the impact on the environment during synthesis 709652-82-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 165 (100 mg, 0.518 mmol) in toluene 15 ml was added 66 (99.7 mg, 0569 mmol). PTSA (196.8 mg 1.03 mmol) was added to the reaction mass, which was then stirred at 120 C. for 12 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 ml.). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was used in the next step with out further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-62-1, its application will become more common.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); 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