Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, 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, name: 2-(2-Chloropyridin-3-yl)acetic acid, blongs to pyridine-derivatives compound. name: 2-(2-Chloropyridin-3-yl)acetic acid

2-chloro-3-pyridineacetic acid 50 g,Prepared into a 25% mass fraction of 2-chloro-3-pyridine sodium acetate solution,And 47 g of a 30% sodium hydroxide solutionSouring (the system may produce some insoluble polymer),Stir evenly after filtration,In the filtrate, 20% of Raney nickel catalyst was added,Heating up to 90-95 ,Through hydrogen reaction,In the atmospheric pressure or 1MPa pressure environment reaction,In the control,After the reaction is completed,After filtering the catalyst,The filtrate was adjusted to pH 4 with hydrochloric acid,Activated charcoal decolorization, desolate, offDry solvent (into a viscous fluid,And there is crystal presence (NaCl)Add 100 grams of anhydrous ethanol, fully dissolved,Filtration, the filtrate is 3-pyridine acetic acid in ethanol solution,The ethanol in the solution was removed (dried,Into a viscous fluid, can be added to the back of the amount of water,Dry the ethanol)Add water 50g, and add hydrochloric acid 35g,After sufficiently salt formation at 50 C,The solvent water is then dried (viscous solid)Cooling to room temperature,Plus 50g of absolute ethanol after washing,After filtration, the solid was rinsed with a portion of ethanol,Dry, that was finished3-pyridine acetic acid hydrochloride47.5 g, purity 99.1%, yield 95.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Red Sun Biochemistry Co., Ltd.; Yue, Ruikuan; Chen, Honglong; Wang, Wenkui; Luo, Chaoran; Chen, Xinchun; Jiang, Jianhua; Ding, Yongshan; Zhong, Jinsong; Wang, Shugang; Zhan, Xinhua; (5 pag.)CN106366034; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 173528-92-2 ,Some common heterocyclic compound, 173528-92-2, molecular formula is C20H18N2O3S, 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 8 (E)-4-[2-[2-[[(p-Hydroxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine In DMF was dissolved 2.00 g of the (E)-4-[2-[2-[[(p-methoxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine obtained in Example 3, followed by addition of 1.91 g of sodium methanethiolate, and the mixture was stirred at 100 C. overnight and then after-treated. The resulting crystals were recrystallized from methanol to provide 0.19 g of the title compound (white powders). m.p. 293-296 C. (decomp.) Elemental analysis for C19 H16 N2 O3 S

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. 173528-92-2, HMN-154, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Shinyaku Company, Limited; US5972976; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-43-6 ,Some common heterocyclic compound, 1122-43-6, molecular formula is C7H9NO, 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 stirred solution of the 2,6-dimethylpyridin-3-ol (500 mg, 4.06 mmol) in DMF (15 mL) in a 50 mL flame-dried RBF, K2CO3 (0.617 g, 4.47 mmol) and MOM-C1 (0.37 mL, 4.87 mmol) were added successively. The solution was stirred at RT overnight. Water (30 mL) was added and the reaction mixture extracted with EtOAc (2 x 20 mL). The organic layer was washed with cold water (2 x 30 mL) and brine (30 mL) and dried over magnesium sulfate and concentrated under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; EMORY UNIVERSITY; MERCER UNIVERSITY; HOWARD UNIVERSITY; UNION UNIVERSITY; GUeNER, Osman; LASSEGUE, Bernard; GRIENDLING, Kathy; XU, Qian; BROWN, David; BOWEN, J. Phillip; KULKARNI, Amol; WATKINS, E. Blake; (73 pag.)WO2019/23448; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1026796-81-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1026796-81-5 as follows.

To a solution of N-(4-bromopyridin-2-yl)acetamide (350 mg, 1.6 mmol) in DCM (20 mL) was added mCPBA (1.26 g, 7.3 mmol) at 0 C. The reaction mixture was allowed to stir at rt for 3 h. The reaction mixture was then diluted with water and saturated K2CO3 solution, and extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to provide N-(4-bromo-1-oxidopyridin-2-yl)acetamide (340 mg, 90%). LCMS (FA): m/z=231.3 (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,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52311-20-3, Adding some certain compound to certain chemical reactions, such as: 52311-20-3, name is 2-Amino-4-ethoxypyridine,molecular formula is C7H10N2O, 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 52311-20-3.

Preparation 62 A mixture of (3-chloro-2-oxobutylidene)triphenylphosphorane (12.7 g) and 3-benzyloxy-4-nitrobenzaldehyde (8.9 g) in dioxane (130 ml) was heated under reflux for 2 hours. The solvent was evaporated in vacuo and the residue was dissolved in isopropyl alcohol (130 ml). To the solution was added 2-amino-4-ethoxypyridine (12.0 g) and the mixture was heated under reflux for 2.5 hours. Evaporation of the solvent gave a residue, which was dissolved in a mixture of ethyl acetate and water. The mixture was adjusted to pH 1 with 6N-hydrochloric acid and the isolated precipitate was collected by filtration. To the precipitate was added a mixture of tetrahydrofuran, ethyl acetate and water, and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate solution with salting-out technique. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated with a mixture of diethyl ether and diisopropyl ether. The precipitate was collected by filtration and dried to give 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-ethoxy-3-methylimidazo[1,2-a]pyridine (3.94 g). mp: 153-154 C. IR (Nujol): 1650, 1635, 1600, 1585 cm-1

According to the analysis of related databases, 52311-20-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5047411; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54-92-2, Adding some certain compound to certain chemical reactions, such as: 54-92-2, name is N’-Isopropylisonicotinohydrazide,molecular formula is C9H13N3O, 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 54-92-2.

A solution of 3-(2′,3′-dimethyl-biphenyl-2-yl)-propionic acid (127 mg, 0.50 mmoles) and isonicotinic acid N’-isopropyl-hydrazyde (ACROS) (167 mg, 0.60 mmoles) in DMF (5 mL) was treated with diisopropylethylamine (0.35 mL, 2.0 mmoles), and PyBroP (350 mg, 0.75 mmoles) at room temperature for 16 h. The reaction mixture was partitioned between 1N NaOH and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with 100% ethyl acetate to afford the product (17 mg, 8%). LC-MS m/e 416.49 (M+H+)

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. 54-92-2, N’-Isopropylisonicotinohydrazide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Michoud, Christophe; US2006/258740; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17117-17-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17117-17-8 as follows.

(4E)-N-Methyl-N-(tert-butoxycarbonyl)-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80-85 C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3*20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluding with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17117-17-8, its application will become more common.

Reference:
Patent; Caldwell, William S.; Dull, Gary M.; Bhatti, Balwinder S.; Hadimani, Srishailkumar B.; Park, Haeil; Wagner, Jared M.; Crooks, Peter A.; Lippiello, Patrick M.; Bencherif, Merouane; US2003/125345; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16727-47-2, Adding some certain compound to certain chemical reactions, such as: 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine,molecular formula is C19H16BrNO2, 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 16727-47-2.

To a stirred solution of 16-1 (5.0 g, 13.5 mmol) in Dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.12 g, 20.2 mmol) and KOAc (2.64 g, 27.0 mmol). The reaction mixture was degassed with argon for 10 minutes. PdCl2(dppf).DCM (1.10 g, 1.35 mmol) was added and the resulting mixture was stirred at 100 oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-5% Ethyl acetate in Hexane) to afford 25-1 (3.5 g, 62%) as a pale yellow solid.

According to the analysis of related databases, 16727-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); 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.92992-85-3, name is 2-Bromo-3,5-dimethylpyridine, molecular formula is C7H8BrN, molecular weight is 186.0491, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8BrN

[0085 -Step e: Preparation of 2′,5′-dichloro-3,5-dimethyl-2,4′-bipyridine [0086] To a solution of 2,5-dichloropyridin-4-ylboromc acid (7.56 g, 40 mmol), 2-bromo- 3,5- dimethylpyridine (5.62 g, 30 mol) in dioxane (60 mL) and H?0 (12 mL) were added Pd(dppf)CI2 (1.35 g, 1.7 mmol) and K :'( ) · 31 >( > (16.2 g, 60 mmol), the mixture was stirred at reflux under N2 atmosphere overnight. TLC showed the reaction was complete. After cooling to room temperature, the mixture was filtered. Water (50 mL) was then added to the filtrate. The mixture was extracted with dichloromethane (150 mL x 3). The combined organic layers were washed with brine (300 mL), dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 20:1 to 10:1) to give title compound (3.1 g, 41%) as a white solid. NMR (400MHz, CDCI3): delta 8.46 (s, 1 H), 8.37 (s, 1 H), 7.47 (s, 1 H), 7.33 (s, 1 H), 2.39 (s, 3H), 2.16 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92992-85-3, 2-Bromo-3,5-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ZHANG, Xiaohu; WO2014/113191; (2014); A1;,
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. 502509-10-6, name is 4-(2-Hydroxyethyl)picolinic acid. A new synthetic method of this compound is introduced below., Formula: C8H9NO3

To a stirred solution of acid 70 (4.76 g, 23.4 mmol) acid in MeOH (104 mL) at 0 C was slowly added thionyl chloride (3.40 mL, 46.8 mmol) and was heated at reflux during 24 h. After cooling at 0 C, thionyl chloride (3.40 mL, 46.8 mmol) was added in second time and heated at reflux during 24 h. Then, the mixture was concentrated in vacuo and a saturated aqueous solution of NaHCO3 was added until basic pH. The aqueous layer was extracted with EtOAc (thrice). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 36 as black oil in 38% yield (1.60 g). The crude product was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) delta 8.43 (d, J = 4.9 Hz, 1H), 7.90 (d, J = 0.9 Hz, 1H), 7.27 (dd, J = 5.0, 1.7 Hz, 1H), 3.88 (s, 3H), 3.84 (t, J = 6.4 Hz, 2H), 3.44 (bs, 1H), 2.83 (t, J = 6.3 Hz, 2H). 13C NMR (75 MHz, CDCl3) delta 165.6, 150.2, 149.3, 147.3, 127.8, 125.8, 61.7, 52.7, 38.2. MS (ESI+): m/z (%): 182 (100) [M+H]+.

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, 502509-10-6, 4-(2-Hydroxyethyl)picolinic acid.

Reference:
Article; Oukoloff, Killian; Coquelle, Nicolas; Bartolini, Manuela; Naldi, Marina; Le Guevel, Remy; Bach, Stephane; Josselin, Beatrice; Ruchaud, Sandrine; Catto, Marco; Pisani, Leonardo; Denora, Nunzio; Iacobazzi, Rosa Maria; Silman, Israel; Sussman, Joel L.; Buron, Frederic; Colletier, Jacques-Philippe; Jean, Ludovic; Routier, Sylvain; Renard, Pierre-Yves; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 58 – 77;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem