Tag: M.W:200-300

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 754230-78-9, name is 3-(Benzyloxy)-5-bromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-(Benzyloxy)-5-bromopyridin-2-amine

Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine from Example 1 6A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g of 3 Amolecular sieve were suspended in 6 1 of ethanol, and the suspension was stirred at reflux for 72 h. The reaction mixture was filtered oil through silica gel and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=9: 1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound.10595] LC-MS (Method 16): R=1.31 mm10596] MS (ESpos): mlz=389 (M+H)j0597] ?H-NMR (400 MHz, DMSO-d5): oe=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 754230-78-9.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (95 pag.)US2016/347770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 175201-94-2, 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. 175201-94-2, name is 4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Example 6 (1,3-Dimethyl-4-morpholin-4-ylpyrazolo[5,4-b]pyridin-5-yl)-N-({[4-fluoro 3-(trifluoromethyl)phenyl]amino}carbonyl)carboxamide (65) A solution of 4-chloro-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carboxylic acid (450 mg) and morpholine (870 mg) in DMF (15 mL) was stirred at room temperature for 5 h, and then concentrated under reduced pressure. The residue was treated with water (10 mL), and the resulting solid was filtered, washed with water, and dried under high vacuum. The solid was suspended in anhydrous dichloromethane (20 mL) and treated with oxalyl chloride (1.0 mL) and anhydrous DMF (0.1 mL). The mixture was stirred at room temperature for 1 h, filtered, and the filtrate was concentrated under reduced pressure. The residue was cooled in an ice-bath and slowly treated with a saturated solution of ammonia in THF (20 mL). The suspension was removed from the ice-bath, stirred at room temperature for 1 h, and filtered. The solid was washed with water and dried under high vacuum to give 1,3-dimethyl-4-morpholin-4-ylpyrazolo[5,4-b]pyridine-5-carboxamide as a white powder. A portion of this material (0.33 g) was dissolved in hot toluene (30 mL) and azeotroped for 1 h.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175201-94-2, 4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Laborde, Edgardo; Robinson, Louise; Meng, Fanying; Peterson, Brian T.; Villar, Hugo O.; Anuskiewicz, Steven E.; Ishiwata, Yoshiro; Yokochi, Shoji; Matsumoto, Yukiharu; Kakigami, Takuji; Inagaki, Hideaki; Jomori, Takahito; Matsushima, Kouji; US2003/96705; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 872619-43-7, 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.872619-43-7, name is Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, molecular formula is C9H7BrN2O2, molecular weight is 255.07, as common compound, the synthetic route is as follows.

Example 7; Methyl 5-[4-(2-morpholin-4-ylethoxy)phenyl]-l^-pyrrolo[2,3-6]pyridine-3-carboxylate; Triisopropyl borate (0.39 mL, 1.7 mmol) was added to a stirred solution of 4-[2-(4-bromophenoxy)ethyl]morpholine (0.163 g, 0.57 mmol; described in: Lednicer, D., et al, J.Med. Chem. 1965, 8, 52-57) in anhydrous tetrahydrofuran (4 mL). The resulting solution wascooled to -70 C and H-butyllithium (1.1 mL, 1.6 M in hexane, 1.76 mmol) was addeddropwise. The mixture was stirred at -70 C for 1 h and was then allowed to warm to roomtemperature. Hydrochloric acid (aq. 2.85 mL, 1 M, 2.85 mmol) was added and the mixturewas stirred for 2 min, followed by addition of sodium carbonate (0.604 g, 5.7 mmol). Afterstirring for another 2 min, methyl 5-bromo-l//-pyrrolo[2,3-6]pyridine-3-carboxylate (0.100 g,0.4 mmol) and [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethaneadduct (0.047 g, 0.057 mmol) were added and the resulting mixture was heated at 65 C overnight. The solvent was evaporated and the residue was purified on a silica gel column usingdichloromethane/methanol, (95:5), as the eluent. Re-crystallization from acetonitrile gave0.048 g (31% yield) of the title compound as crystals:’H NMR (CDC13, 400 MHz) 8 10.06 (m, 1 H), 8.57 (m, 2 H), 8.06 (s, 1 H), 7.58 (m, 2 H),7.02 (m, 2 H), 4.29 (m, 2 H), 3.94 (s, 3 H), 3.85 (m, 4 H), 2.99 (m, 2 H), 2.77 (m, 4 H).

Statistics shows that 872619-43-7 is playing an increasingly important role. we look forward to future research findings about Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 50488-42-1, 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. 50488-42-1, name is 2-Bromo-5-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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.

EXAMPLE 301A 5-(trifluoromethyl)-2-pyridinecarbonitrile Copper (I) cyanide (14.1 g) and 2-bromo-5-trifluoromethylpyridine (3.00 g, 13.3 mmol) in dry DMSO (70 mL) were combined and heated at 180 C. for 2 hours, cooled, and poured into NH4OH (3M). The mixture was then extracted with ethyl acetate (3*500 mL), washed with water (1*200 mL), dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound. 1H NMR (DMSO, 300 MHz) delta 8.22 (m, 1H), 8.42 (m, 1H), 9.01 (s, 1H).

According to the analysis of related databases, 50488-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US6933311; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130722-95-1, Adding some certain compound to certain chemical reactions, such as: 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine,molecular formula is C12H10BrNO, 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 130722-95-1.

3-Benzyloxy-5-bromopyridine (4.73 g, 18.0 mmol) was dissolved in tetrahydrofuran (25 rnL) and cooled to 0 0C.Isopropylmagnesiumchloride (10 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hrs at room temperature. N.N-dimethylformamide (3 mL) in tetrahydrofuran (10 mL) was added and stirring was continued for an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3-benzyloxy-5-formylpyridine (2.00 g, 53%) as white solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.72 (d, IH), 8.66 (d, IH), 7.84 (m, IH), 7.42-7.48 (m, 5H), 5.28 (s, 2H).

According to the analysis of related databases, 130722-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one

2-Hydroxy-3-nitro-5-trifluoromethylpyridine (8.8 g, 42.3 mmol) was added to a mixture of phosphorous oxychloride (4.2 mL, 45.9 mmol) and phosphorous pentachloride (9.6 g, 46.1 mmol) at 60 C. The reaction mixture was then heated under nitrogen at 80 C. overnight. The resulting dark product mixture was allowed to cool to room temperature and was poured into ice/water. The mixture was extracted with ether and the ether extract was washed with water and brine. After drying over magnesium sulfate, the solvent was removed to leave a dark oil which was subjected to flash chromatography on silica gel eluding with chloroform. Fractions containing only the desired product were combined and concentrated to leave a brown oil (5.0 g, 52%). 1 H NMR (DMSO-d6): delta9.20 (s, 1H), 9.07 (s, 1H).

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, 33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one.

Reference:
Patent; Pfizer Inc; US5811432; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2,3-Dichloro-5-(trifluoromethyl)pyridine

To a solution of ethyl 3- [2-hydroxy-4- (2- methoxyethoxy) phenylJbutanoate (5.50 g) in N, N- dimethylformamide (40 ml) was added sodium hydride (60% in oil, 932 mg) under ice-cooling, and the mixture was EPO subsequently stirred for 30 min. Then, 2, 3-dichloro-5- ‘ (trifluoromethyl) pyridine (3.0 ml) was added, and the mixture was stirred at room temperature for 2 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried (MgSO4) , filtrated and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (hexane alone to 35:65, v/v) to give ethyl 3- [2-{ [3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}-4-(2- methoxyethoxy) phenylJbutanoate (7.80 g, yield: 87%) as a yellow oil.1H-NMR (300 MHz, CDCl3)S: 1.16 (3 H, t, J = 7.2 Hz), 1.22 (3 H, d, J = 7.0 Hz), 2.39 – 2.50 (1- H, m) , 2.56 – 2.70 (1 H, m) , 3.23 – 3.38 (1 H, m) , 3.43 (3 H, s) , 3.65 – 3.79 (2 H, m) , 3.96 – 4.19 (4 H, mj , 6.66 (1 H, d, J = 2.6 Hz), 6.85 (1 H, dd, J = 8.7, 2.6 Hz), 7.18 – 7.29 (1 H, m) , 7.98 (1 H, d, J = 2.1 Hz), 8.25 (1 H, d, J = 1.1 Hz).

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, 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1082040-63-8, Adding some certain compound to certain chemical reactions, such as: 1082040-63-8, name is 3-Iodo-1H-pyrazolo[3,4-c]pyridine,molecular formula is C6H4IN3, 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 1082040-63-8.

To a solution of 3-iodo-lH-pyrazolo[3,4-c]pyridine (6.0 g, 24.5 mmol, 1.0 eq.) and K2C03 (4.0 g, 29.4 mmol, 1.2 eq.) in DMF (40 mL) was added tert-butyl 2-bromoacetate (4.78 g, 24.5 mmol, 1.0 eq.). The resulting mixture was stirred at r.t. for 2 h, then poured into water (200 mL), extracted with EtOAc (200 mL x 3). The combined organic layers were dried and concentrated under vacuum. The residue was purified by column chromatography (PE/EtOAc=3: l) to provide tert-butyl 2-(3-iodo-lH-pyrazolo[3,4- c]pyridin-l-yl)acetate as a yellow oil (6.0 g, 68.0% yield).

According to the analysis of related databases, 1082040-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (297 pag.)WO2018/229543; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1152617-24-7, Adding some certain compound to certain chemical reactions, such as: 1152617-24-7, name is 3-Chloro-4-iodopyridin-2-amine,molecular formula is C5H4ClIN2, 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 1152617-24-7.

To a mixture of Zl7c (6.95 kg, assay 72%, 27.23 mol) in l,4-dioxane (72 L) was added Xantphos (233 g, 411 mmol, 0.015 eq), Pd2(dba)3 (186 g, 206 mmol, 0.0075 eq), Zl7b (7.13 kg, 28.02 mol) and DIPEA (7.02 kg, 54.46 mol). The system was vacuated and purged with nitrogen gas three times. The mixture was stirred at 65 C for 16 h under N2. The mixture was cooled to RT and water (50 L) was added, filtered. The cake was washed with EA (25 L). The filtrate was extracted with EA (4 x 20 L). The organic phase was concentrated in vacuum to offer the crude product which was combined with the cake. Then DCM (60 L) was added to the crude product and stirred at 25-30C for l8h and then filtered. The filter cake was slurried with CH2CI2 (30 L) for 4 hrs and filtered. The filter cake was slurred in CH2CI2 (30 L) for 16 hrs and filtered. Then the filter cake was dried in vacuum to give Z17a (3-((2-amino-3-chloropyridin-4-yl)thio)-6-chloropyrazin-2-amine; 9.1 kg, 84 %) as light yellow solid. NMR (400 MHz, DMSO-d6) d = 7.89 (s, 1H), 7.7 (d, J= 7.6 Hz, 1H), 7.18 (bs, 2H), 6.40 (bs, 2H), 5.97 (d, J= 7.6 Hz, 1H).

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. 1152617-24-7, 3-Chloro-4-iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; LU, Gang; WAN, Yinbo; WANG, Jianhua; WU, Quanbing; ZHANG, Hao; (116 pag.)WO2020/65453; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 882521-63-3, 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.882521-63-3, name is 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, molecular formula is C6H5BrN4, molecular weight is 213.04, as common compound, the synthetic route is as follows.

General procedure: To a microwave tube was added [1,2,4]triazolo[1,5-a]pyridin-2-amine 13 (1 equiv), K2CO3 (2.0 equiv), Pd(PPh3)4 (0.056 equiv), and the corresponding boronic acid (1.5 equiv). 5 mL of EtOH:H2O (1:1) was used as solvent, and the microwave conditions employed were 150 C for 30 min. After solvent evaporation, the product was purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 100%) in n-hexane or MeOH (0 – 10%) in DCM to afford the desired compound 16 (adapted from 4).

The chemical industry reduces the impact on the environment during synthesis 882521-63-3, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem