Category: pyridine-derivatives

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. 52334-90-4, name is 3-Methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 52334-90-4

3,4-dichlorobenzenesulfonyl chloride (1 mmol) and 3-methoxypyridin-4-ylamine (1 mmol) were reacted without solvent at 130 C for 4 hours, then cooled and dissolved in a mixture of NaOH (1 M, 10 mL) and methanol (10 mL). Then water and dichloromethane were added and the aqueous phase was collected. The aqueous phase was adjusted to pH 3-4 with acetic acid and then extracted with ethyl acetate. The organic phase was evaporated and the residue was subjected to column chromatography (Si02, ethyl acetate) to give N-(3-methoxypyridin-4-yl)-3,4-dichlorobenzenesulfonamide. The reaction of this intermediate with boron tribromide was as described for N-(6-chloro-4- hydroxypyridin-3-yl)-3,4-dichlorophenyl-methanesulfonamide except that a precipitate formed during the partition between dichloromethane and aqueous sodium hydroxide at pH 13. Without separating the phases, pH was adjusted to 3 with 1 M HC1 and the two- phase mixture was filtered in order to collect the precipitate. The precipitate (30 mg, 9%) was the title compound according to nmr and mass

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, 52334-90-4, 3-Methoxypyridin-4-amine.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); 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.872602-74-9, name is 6-Cyanopicolinic acid, molecular formula is C7H4N2O2, molecular weight is 148.1189, as common compound, the synthetic route is as follows.name: 6-Cyanopicolinic acid

6-Cyano-pyridine-2-carboxylic acid (compound F2) (250 mg, 1.6 mmol) is dissolved in ethanol (100ml), concentrated hydrochloric acid (1 mL) and Pd/C (150 mg) are added and the mixture ishydrogenated at 3 bar hydrogen pressure for 6 h. The catalyst is filtered of and the crude product istransferred to the next step without any purification. Yield: 255 mg (85 %) mp: 214-221 C

At the same time, in my other blogs, there are other synthetic methods of this type of compound,872602-74-9, 6-Cyanopicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ALTANA PHARMA AG; WO2006/589; (2006); 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. 1658-42-0, name is Methyl 2-(pyridin-2-yl)acetate. A new synthetic method of this compound is introduced below., Formula: C8H9NO2

General procedure: A mixture of phenylethynylbromide (1a) (1.0 mmol), ethyl2-pyridylacetate (2a) (0.6 mmol), AgNO3 (34.0 mg, 0.2 mmol, 0.2 equiv.), DABCO(70.0 mg, 1.0 mmol, 1.0 equiv.) in DMSO (3.0 mL) in a test tube (25 mL)equipped with a magnetic stirring bar. The mixture was stirred at 100 oCfor 12 h. After the reaction was completed, the mixture was washed with brineand extracted with ethyl acetate. The organic layer was dried (MgSO4),concentrated in vacuum and purified by flash silica gel chromatography usingpetroleum ether/ethyl acetate 10:1 to give the desired products.

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, 1658-42-0, Methyl 2-(pyridin-2-yl)acetate.

Reference:
Article; Zeng, Wei; Wu, Wanqing; Jiang, Huanfeng; Sun, Yadong; Chen, Zhengwang; Tetrahedron Letters; vol. 54; 35; (2013); p. 4605 – 4609;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116986-13-1, 3-(Bromomethyl)picolinonitrile, 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, Recommanded Product: 3-(Bromomethyl)picolinonitrile, blongs to pyridine-derivatives compound. Recommanded Product: 3-(Bromomethyl)picolinonitrile

Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (0.104 g, 0.39 mmol), 3-bromomethyl-pyridine-2-carbonitrile (0.115 g, 0.58 mmol), KI (23 mg, 0.14 mmol), and DIPEA (0.15 mL, 0.86 mmol) in DMF (4 mL) was heated at 60 C. for 20 hours. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-CH3OH-NH4OH) provided 133 mg (88%) of 3-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2’H-cis-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-pyridine-2-carbonitrile as a tan solid.

The synthetic route of 116986-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Gang; Crawford, Jason; Skerlj, Renato; US2005/154201; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113770-88-0, 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.113770-88-0, name is 3-Fluoro-4-cyanopyridine, molecular formula is C6H3FN2, molecular weight is 122.1, as common compound, the synthetic route is as follows.

3-Fluoro-isonicotinonitrile (0.50 g, 4.10 mmol) was dissolved in ethanol (8 mL) and treated with hydrazine hydrate (0.31 g, 6.1 mmol). After stirring at 70 C for 16 h, the mixture was cooled to RT and concentrated in vacuo and dried to yield the title compound (0.66 g, 100% of theory). LC-MS (Method 2B): Rt = 0.51 min, MS (ESIPos): m/z = 135 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 113770-88-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; CANCHO-GRANDE, Yolanda; BEYER, Kristin; ROeHRIG, Susanne; KOeLLNBERGER, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; WO2015/67549; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, 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, Recommanded Product: 571189-16-7, blongs to pyridine-derivatives compound. Recommanded Product: 571189-16-7

Add to the reaction flask4- (6-nitropyridin-3-yl) piperazine-1-tert-butylcarboxylate (3.4 g, 11 mmol,First step), and palladium on carbon (10%, 400 mg)Ethyl acetate / ethanol (100 mL, 1: 1).The mixture was stirred at room temperature for 12 hours in a hydrogen atmosphere.Filtered and concentrated under reduced pressure to give the title compound (2.8 g, white solid) in 93% yield.

The synthetic route of 571189-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); 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

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.54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.SDS of cas: 54221-96-4

2-(3,4-dichlorophenyl)acetonitrile (3.50 g, 18.8 mmol) was taken up in THF (30 mL) and diethyl ether (30 mL), and cooled to -78 °C in an acetone-dry ice bath. BuLi (8.1 mL, 20 mmol, 1.6 M in hexane) was added drop-wise, and the temperature was maintained below -60 °C. Once the last drop had been added, the reaction was allowed to stir for 15 minutes. This solution became orange clear. 6- methoxypicolinaldehyde (2.3 mL, 19 mmol) dissolved in THF (20 mL) was added slowly drop-wise, and the temperature was maintained below -60 °C. Solution was dark brown / black clear at this point and was allowed to stir for 1.5 hours at -75 °C. The reaction was quenched with acetic acid (1.6 mL, 28 mmol) dissolved in 5 mL of diethyl ether, added drop-wise while the reaction was cooled in the dry ice acetone bath. The temperature was maintained below -60 °C. LCMS revealed mostly one peak with the desired mass. The reaction was worked up by adding 100 mL of water, and layers were separated. The aqueous phase was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSC , and concentrated in vacuo to afford 8.14 grams of a clear amber oil. LCMS revealed a peak that was consistent with desired material. The material was absorbed onto silica gel and ran through an ISCO 80 gram column, eluting with CH2C12 / EtOAc. The broad peak looked to be a mixture of diastereomers in a ratio around 1.5:1. It was not determined which diastereomeric pair is the more predominant pair (0.988 g). The spiked shoulder from that broad peak looked to be a mixture of diastereomers in a ratio around 4: 1 (4.39 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54221-96-4, 6-Methoxypicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; RICHELSON, Elliott; FAUQ, Abdul H.; CARLIER, Paul R.; MONCEAUX, Christopher J.; WO2014/159251; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-75-0, 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. 17228-75-0, name is 2,6-Dichloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

a) Synthesis of 2,6-dichloro-4-methoxy-pyridine-3-carboxylic acidTo a solution of 4.0 g (22.5 mmol) 2,6-dichloro-4-methoxy-pyridine in THF (20 ml) was added 10.0 ml (2.47 M in hexane, 24.7 mmol) n-butyllithium at -78 C. After stirring for 1 h at -78 C excess dry ice was added and the mixture was allowed to warm to RT. Then the mixture was acidified with 6N aqueos hydrochlorid acid to pH 3-4 followed by extraction with EtOAc. The organic layer was dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1 ) provided 3.5 g (15.8 mmol, 70%) 2,6-dichloro-4-methoxy- pyridine-3-carboxylic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17228-75-0, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 105596-63-2 ,Some common heterocyclic compound, 105596-63-2, molecular formula is C7H7NO3, 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.

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride 2.7-hydrate (1.06 g, 3.26 mmol) was added to a solution of 2-methoxy-isonicotinic acid (500 mg, 3.26 mmol) and 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (669 mg, 2.97 mmol) in EtOH (8.0 ml) at room temperature, and the mixture was stirred for 46.5 hours. An aqueous NaHCO3 solution was added to the reaction mixture, followed by extraction with AcOEt three times. The organic layers were washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (CH2Cl2/MeOH = 99:1 to 95:5) to give 4-cyano-4-[(2-methoxy-pyridine-4-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless form (901 mg, 84%). MS (ESI) m/z = 361 (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. 105596-63-2, 2-Methoxyisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2433940; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem