Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 19235-89-3, 4-Chloropyridine-2-carbonitrile, 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, HPLC of Formula: C6H3ClN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3ClN2

To a suspension of 4-chloropyridine-2-carbonitrile (2.3 g, 16.6 mmol) in DMF (100 mL) was added cesium carbonate (16.3 g, 50.0 mmol) and 3-(4-hydroxy-phenyl)propanoic acid (3.03 g, 18.3 mmol). The reaction was heated to 50 C. for 3 days. The mixture was cooled to rt, concentrated, and then taken up in 300 mL of water. The pH was adjusted to 3 by the dropwise addition of oxalic acid and a precipitate formed. The precipitate was filtered to give the title compound as a cream solid (4.17 g, 95%). LCMS: Method FA, Rt=1.49 min, [MH+=269].

The synthetic route of 19235-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2006/160803; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135900-33-3, 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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

[0294] A stirred solution of 7-bromo-6-fluoroquinoline Int-6 (Example 123) (100 mg, 0.442 mmol), 6-(trifluoromethoxy)pyridin-3-amine (157 mg, 0.884 mmol, 2.0 eq) and Na2CC>3 (112 mg, 0.884 mmol) in dry acetonitrile (2 mL) was degassed with Argon gas in a microwave vessel for 15 min. Then Mo(CO)6 (117 mg, 0.442 mmol, 1.0 eq), T3u3PHBF4 (15.3 mg, 0.05 mmol 0.12 eq) and Pd(OAc)2 (10 mg, 0.044 mmol, 0.1 eq) were added to this mixture, and degassing was continued for additional 10 min. The reaction mixture was irradiated in microwave at 90 C for 2 hrs. The progress of the reaction was monitored by LCMS and TLC. Upon completion, the reaction mixture was concentrated in vacuo. The crude product was purified by silica gel column chromatography using 50% EtOAc in petroleum ether as eluent to give 25 mg (16% yield) of the desired compound 129 as a pale-yellow solid. 99.2 % HPLC purity at 215 nm. 1H NMR (400 MHz, CDC13): delta 9.03- 9.02 (dd, J = 4.0 Hz, 1.6 Hz, 1H), 8.97-8.99 (d, J = 7.6 Hz, 1H), 8.59 (s, 1H), 8.55 (s, 1H), 8.47-8.49 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.45-8.46 (d, J = 2.4 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.61-7.64 (d, J = 12.8 Hz, 1H), 7.56-7.52 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.12-7.10 (d, J = 8.0 Hz, 1H). 99.7% purity by LCMS; MS (ESI) m/z =352.14 [M+H]+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 3430-16-8, 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.3430-16-8, name is 3-Bromo-5-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

The following are successively introduced into a microwave tube: 469.80 mul (4.07 mmol) of 3-bromo-5-methylpyridine in 20 mL of H2O/DMF: (1/3: v/v), 2.03 mL (5.70 mmol) of tributyl(1-ethoxyvinyl)tin, 57.12 mg (81.38 mmol) of bis(triphenylphosphine)palladium(II) chloride, 1.12 g (8.14 mmol) of potassium carbonate. After irradiating with microwaves for 1 hour at 110 C., the reaction mixture is evaporated to dryness and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is taken up in a solution consisting of 6 mL of methanol and 1 mL of 1 N hydrochloric acid. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness and the residue is taken up in saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 160 mg of 1-(2-methylpyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 136 tr (min)=0.38 1H NMR (300 MHz, delta in ppm, DMSO-d6): 2.58 (s, 3H), 2.61 (s, 3H), 7.38 (m, 1H), 8.2 (m, 1H), 8.57 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 3430-16-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; El-Ahmad, Youssef; Filoche-Romme, Bruno; Ganzhorm, Axel; Marciniak, Gilbert; Muzet, Nicolas; Ronan, Baptiste; Vivet, Bertrand; Zerr, Veronique; US2015/183804; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 121643-44-5, 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.121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, molecular weight is 177.1239, as common compound, the synthetic route is as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridineTo 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

Statistics shows that 121643-44-5 is playing an increasingly important role. we look forward to future research findings about 2-Methoxy-3-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; FERNANDES GOMES DOS SANTOS, Paulo Antonio; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SOLDERMANN, Nicolas; STOWASSER, Frank; TUFILLI, Nicola; ZECRI, Frederic; WO2013/1445; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1142197-14-5, 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. 1142197-14-5, name is 2-Bromo-5-cyclopropylpyridine. A new synthetic method of this compound is introduced below.

Step 1 : 2-bromo-5-cyclopropylpyridine -oxide (245) [0747] To a solution of 2-bromo-5-cyclopropylpyridine (2.0 g, 10.1 mmol) in CHCI3 (10 mL) was added m-CPBA (2.62 g, 15.2 mmol). The reaction was stirred at room, temperature overnight. The mixture was diluted DCM and washed with 5% aq. NaHCC solution and brine. The organic layer was dried over anhydrous NaiSCH, filtered and concentrated. The residue was purified by column chromatography on silica gel eiuted with PE/EtOAc (30: 1 to 1 : 1) to give compound 245 (2.12 g, 98.6 % yield) as a white solid. LC/MS (ESI) m/z: 214 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142197-14-5, 2-Bromo-5-cyclopropylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (386 pag.)WO2017/35355; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145335-90-6 ,Some common heterocyclic compound, 145335-90-6, molecular formula is C8H7ClN2O2, 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.

Method 2: To imidazo[l,2-alpha]pyridine-8-carboxylic acid hydrochloride (15.0 g, 76 mmol), toluene (80 mL) was added followed by thionyl chloride (17.4 g, 146 mmol). To the resulting mixture, N^N-dimethylformamide (1.15 mL) was added. Gas evolution was noticed and the mixture was stirred at ambient temperature for 30 min and then was heated to 50 0C overnight (18 h). The reaction mixture was then cooled to room temperature for 30 min and the product was filtered and washed with isopropyl acetate (40 mL) followed by ethyl acetate (40 mL). The white solid was dried under reduced pressure to afford the title compound (13.4 g, 82%). The compound was used without further purification in step E.

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. 145335-90-6, Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); 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. 77618-99-6, name is 2-Amino-5-(methylthio)pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-5-(methylthio)pyridine

Step 4 To 112 muL (1.05 mmol) of 4-fluorobenzaldehyde and 147 mg (1.05 mmol) of 2-amino-5-methylthio-pyridine, dissolved in 6 mL dichloromethane was added 334 mg (1.57 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 4 h. The mixture was then partitioned between ethyl acetate and brine, dried over MgSO4 and concentrated. Purification by column chromatography, eluding with ethyl acetate/hexane, provided 185 mg product, 2-[(4-fluorobenzyl)amino]-pyridin-5-yl methyl sulfide, pure by 1H NMR.

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, 77618-99-6, 2-Amino-5-(methylthio)pyridine.

Reference:
Patent; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Smith, David Bernard; Walker, Keith Adrian; US2002/52349; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116308-35-1, 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. 116308-35-1, name is 2-(Trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

General procedure: The appropriate substituted pyridine aldehyde (10 mmol) was dissolved in ethanol (20 mL) and sodium metabisulfite (15 mmol) in 5 mL water was added in portion over 5 minutes.The reaction mixture was stirred at room temperature for 1 h, and subsequently stirred at 4oC overnight and the formed precipitate was filtered and dried to get sodium bisulfite adducts.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116308-35-1, 2-(Trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Ali, Mohamed Ashraf; Osman, Hasnah; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Masand, Vijay H.; Panneerselvam, Theivendren; Letters in drug design and discovery; vol. 13; 7; (2016); p. 691 – 696;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 393-55-5, 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. 393-55-5, name is 2-Fluoronicotinic acid, molecular formula is C6H4FNO2, 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.

Weigh 10g (70.87mmol)2-fluoro nicotinic acid solubleIn 330mL anhydrous tetrahydrofuran,Stir in an ice bath and slowly add 4.3 g (113.07 mmol) of LiA1H4 in small portions.Generate a lot of air bubbles, with the increase in the amount of LiA1H4 added,The reaction solution was cloudy with white turbidity and yellow.After the addition, the reaction is continued for 20 minutes. The TLC monitors and the reaction is complete. Slowly add 10.6 mL of water to quench the reaction.A large amount of bubbles and solids were generated, and the mixture was suction-filtered. The solvent was evaporated under reduced pressure to give 7.78 g of a yellow liquid, which was used.

According to the analysis of related databases, 393-55-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Li Song; Zheng Zhibing; Lin Feng; Gong Zehui; Lu Xinqiang; Zhou Xinbo; Zhong Wu; Xiao Junhai; Xie Yunde; Li Xingzhou; Wang Xiaokui; (16 pag.)CN107964018; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5006-66-6, 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. 5006-66-6, name is 6-Oxo-1,6-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

31.1 6-hydroxy-nicotinic acid ethyl ester To a 100mL three-necked flask, 0.84g (0.006 mol) of 6-hydroxynicotinic acid, 30mL of anhydrous ethanol were added, 3mL of concentrated sulfuric acid was added dropwise slowly, refluxed overnight, evaporated under vacuum to remove excessive ethanol, the residue was poured into water, extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate, dried with anhydrous sodium sulfate, and concentrated to obtain 0.8g of 6-hydroxy-nicotinic acid ethyl ester. Yield: 80percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5006-66-6, its application will become more common.

Reference:
Patent; Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China; EP1900735; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem