Category: pyridine-derivatives

Related Products of 51285-26-8 ,Some common heterocyclic compound, 51285-26-8, molecular formula is C6H8ClN3, 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 157.8 g. (1.0 mol) of 2-pyridinecarboxamidine hydrochloride 23, 54.2 g (1.0 mol) of sodium methoxide in 400 ml of dry methanol was stirred for 30 minutes. The sodium chloride was filtered and the filtrate was concentrated to dryness. The residue and 83 g (1.0 mole) of 3-methoxyacrylonitrile 24 were heated (100-160°) together for 3 hours, at this point the evolution of ethanol had stopped and the melt had started to crystallize. The product 25 was cooled to room temperature, suspended in methanol, filtered and dried to obtain 25 125.6 g, (73percent yield).

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. 51285-26-8, Picolinimidamide hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHY THERAPEUTICS LLC; HADARI, Yaron R.; CARTA, Luca; SCHMERTZLER, Michael; WILLIAMS, Theresa M.; REYNOLDS, Charles H.; HUTCHESON, Rebecca; (1452 pag.)WO2018/237084; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92992-85-3, 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 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 11b was prepared from 2-bromo-3,5-dimethylpyridine (9b) and 10 in a manner similar to that described for compound 11a, with a yield of 68% as a brown syrup. 1H NMR(DMSO-d6) d 2.29 (s, 3H), 2.30 (s, 3H), 4.55 (d, 2H, J = 5.7 Hz),5.21 (t, 1H, J = 5.7 Hz), 7.38 (d, 2H, J = 8.3 Hz), 7.47 (d, 2H,J = 8.3 Hz), 7.52 (br s, 1H), 8.30 (br s, 1H); MS (ESI) m/z 214 [M+H]+.

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Narazaki, Fumie; Shiina, Yasuhiro; Seo, Ryushi; Amano, Yasushi; Mihara, Takuma; Moriguchi, Hiroyuki; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3351 – 3367;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.

General procedure: 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (Intermediate C, 80mg, 0.30mmol) was dissolved in DMF (lmL) and potassium 2-methylpropane-2-olate (1M in THF, 0.33mL, 0.33mmol) was added dropwise. The mixture was stirred for 5min and a solution of 3-(bromomethyl)-5-methylisoxazole (63.2mg, 0.36mmol) in DMF (0.5mL) was added. The resulting mixture was stirred for 30min and directly purified by column chromatography (Si02, hexane/ethyl acetate). Fraction containing the product were concentrated under reduced pressure and further purified by reversed phase flash chromatography (C18, acetonitrile/water) to yield 3-(3-(4-((lH-pyrazol-l-yl)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine (7lmg, 0.20mmol, 66%) as a white solid. 400 MHz l NMR (CDCl3) d 8.13 (s, 1H), 7.70 (dd , J= 7.7, 1.8 Hz, 1H), 7.24 – 7.16 (m, 2H), 6.98 – 6.89 (m, 2H), 6.70 (dd, J= 7.7, 4.8 Hz, 1H), 6.23 (s, 1H), 6.10 (d, J= 1.1 Hz, 1H), 5.44 (s, 2H), 5.09 (s, 2H), 3.99 (s, 2H), 2.42 (d, .7= 0.9 Hz, 3H). MS: 363.3 [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,135450-23-6, its application will become more common.

Reference:
Patent; AMPLYX PHARMACEUTICALS, INC.; TRZOSS, Michael; COVEL, Jonathan; SHAW, Karen Joy; WEBB, Peter; (240 pag.)WO2019/113542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To degassed dioxane (10mL) were added sequentially 5- trifluoromethylpyridin-3-amine (2) (309mg, 1.9mmol), 2-chloropyrazine (1) (0.26mL, 2.86mmol), Pd2(dba)3 (52mg, 0.06mmol), XantPhos (66mg, 0.1 1 mmol) and Cs2C03 (1.24g, 3.8mmol) with continued degassing. The reaction mixture was heated up to 90C overnight. An additional portion of 2-chloropyrazine (0.17ml_, 1.91 mmol) was then added and the reaction mixture was heated up to (0304) 90C overnight. Once cooled down to rt, it was poured into H20 (20ml_) and extracted with EtOAc (3 x 20ml_). The combined organic extracts were dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-1 :2) gave a residue which was re- dissolved in CH2CI2/MeOH (4:1 , 50ml_) and swirled with MP-TMT resin (440mg, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo to yield (3) as a yellow solid (202mg, 44%). (0305) LCMS (ES): Found 241.0 [M+Hf. (0306) 1H NMR (300 MHz, DMSO-cf6), d: 10.14 (s, 1 H), 9.00 (d, J=2.4 Hz, 1 H), 8.69 (t, J= 2.0 Hz, 1 H), 8.52 (d, J=0.9 Hz, 1 H), 8.32 (d, J=1.5 Hz, 1 H), 8.25 (dd, J= 2.8, 1.5 Hz, 1 H), 8.08 (d, J= 2.8 Hz, 1 H). (0307) 19F NMR (282 MHz, DMSO-cf6), d: -61.09 (s, 3F).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823221-93-8, 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.

Prepared using General Procedure 17: To a stirred a solution of 5- bromo-2-chloro-4-(trifluoromethyl)pyridine (150 mg, 0.576 mmol) in acetonitrile (2 mL) was added sodium iodide (518 mg, 3.45 mmol). The reaction mixture was heated to 40C and acetyl chloride (26.0 mg, 0.345 mmol) was added. The reaction mixture was stirred at 40C for 90 min. Once cooled, the reaction was quenched with NaHC03 (5 mL) and extracted with EA (3 x 5 mL). The combined organics were washed with brine (10 mL), dried over MgS04 and concentrated to give 80.0 mg (40%) of 5-bromo- 2-iodo-4-(trifluoromethyl)pyridine as a white crystalline solid which was used in the subsequent step without purification. LCMS-ESI (m/z) calculated for C6H2BrF3IN: 351.9; found 352.5 [M+H]+, tR = 3.91 min. (Method 1).

Statistics shows that 823221-93-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; RECEPTOS, INC.; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam, R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; WO2013/90454; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-03-6 ,Some common heterocyclic compound, 84487-03-6, molecular formula is C5H4ClN3O2, 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.

General procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH (20 mL). After N2H4 .H2O(4.0 mmol) was added the color of the catalyst was turned to black rapidly in the same way as reducing with NaBH4 . This color change means formation of palladium nanoparticles43 TAPEHA-PdNPs as mentioned above. After being stirred for 20 min at room temperature and atmospheric pressure, the catalyst was removedby ltering and EtOH was removed under a vacuum.

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. 84487-03-6, 6-Chloro-5-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Genc, Hayriye; Zengin, Mustafa; Kuecuekislamo?lu, Mustafa; Imamoglu, Mustafa; Toplan, Hueseyin Oezkan; Arslan, Mustafa; Turkish Journal of Chemistry; vol. 41; 5; (2017); p. 784 – 792;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H9N3O

General procedure: To a 1 dram vial was added 2-substituted-4-phenoxy intermediate 25 (0.066mmol), substituted aminopyridine (0.165mmol), DMF (1mL) and a 60 % dispersion of sodium hydride (0.132mmol) in mineral oil. The resulting reaction mixture was stirred at room temperature for 1h. An aliquot was diluted with wet methanol and analyzed by LCMS. The reaction mixture was quenched with wet DMF and purified by reverse phase HPLC to obtain compound 26.

With the rapid development of chemical substances, we look forward to future research findings about 75279-39-9.

Reference:
Article; Harikrishnan, Lalgudi S.; Warrier, Jayakumar; Tebben, Andrew J.; Tonukunuru, Gopikishan; Madduri, Sudhakara R.; Baligar, Vishweshwaraiah; Mannoori, Raju; Seshadri, Balaji; Rahaman, Hasibur; Arunachalam; Dikundwar, Amol G.; Fink, Brian E.; Fargnoli, Joseph; Fereshteh, Mark; Fan, Yi; Lippy, Jonathan; Ho, Ching-Ping; Wautlet, Barri; Sheriff, Steven; Ruzanov, Max; Borzilleri, Robert M.; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1026 – 1034;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-43-6, 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 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 3-hydroxy-2,6-dimethylpyridine (20 mg, 0.17 mmol) in DMF (1.4 mL) is added NaH (95%, 5 mg, 0.21 mmol). The mixture is stirred for about 15 minutes before benzylchloride 3a4 (75 mg, 0.14 mmol) is added. The mixture is stirred at RT overnight. Methanol (0.5 mL) and LiOH (60 mg, 1.4 mmol) are added and the mixture is further stirred at RT overnight. The mixture is acidified with AcOH and purified by preparative HPLC to isolate compound 1058.

According to the analysis of related databases, 1122-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/18656; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886371-28-4, 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. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine, molecular formula is C7H4BrClN2, 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.

General procedure: To an oven dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), halide/pseudohalide (1 equiv),boron coupling partner (1 equiv), and Cs2CO3 (3 equiv). Thevessel was then capped and purged with N2 before addition ofCyrene (1 mL, 0.25 M) and H2O (1.8 mL). The reaction mixturewas heated to 50 C and maintained at this temperature withstirring for 5 h before the vessel was vented and decapped. Thesolution was then diluted with Et2O (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the title compound.

According to the analysis of related databases, 886371-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wilson, Kirsty L.; Murray, Jane; Jamieson, Craig; Watson, Allan J. B.; Synlett; vol. 29; 5; (2018); p. 650 – 654;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72093-03-9, 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.72093-03-9, name is 3-Chloro-2-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.

To a solution of 3-chloro-2-methylpyridine (0.367 g, 2.88 mmol) in THF (10 mL) was added 0.65 M (2,2,6,6-tetramethylpiperidin-1-yl)zinc(II) lithium chloride (6.65 ml, 4.32 mmol) at ft. The resulting yellow solution was stirred at sametemperature for 1 h, scandium trifluoromethanesulfonate (0.057 g, 0.115 mmol) was added and stirred at room temperature for 15 mm. A microwave vial was charge with 3 -(8-(bis(4-methoxybenzyl)amino)-2-bromo- [1 ,2,4jtriazolo[ 1 ,5-ajpyrazin-6- yl)benzonitrile (0.64 g, 1.152 mmol), palladium acetate (0.021 g, 0.092 mmol) and 2?-(dicyclohexylphosphino)-N,N,N?,N?-tetramethylbiphenyl-2,6-diamine (0.080g, 0.184 mmol) was evacuated under high vacuum and backfilled with nitrogen. The mixture was cooled to 0 C and the zinc reagent was added slowly via syringe. Afier addition, the reaction was heated to 60 C for lh. The reaction solutionwas partitioned between EtOAc and sat. NH4C1 solution. The layers were separated and the aqueous extracted further with EtOAc (2x). The combined organicswere washed with water and brine, dried over MgSO4, and concentrated. The resulting residue was purified via flash chromatography to afford the product. LC-MS calculated for C34H29C1N702 (M+H): mlz = 602.2; found 602.2.

The chemical industry reduces the impact on the environment during synthesis 72093-03-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem