Pyridine-derivatives

Reference of 626-60-8, 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 626-60-8, name is 3-Chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 3-Chloro-N-(4-chlorophenyl)pyridine-4-carboxamide. A solution of 3-chloropyridine (1.00 mL, 10.5 mmol) in THF at -78 C. was treated dropwise with a solution of lithium diisopropylamide in THF [freshly prepared by addition of butyllithium (7.21 mL, 11.5 mmol) to diisopropylamine (11.5 mmol)]. After 0.25 h, the mixture was treated with carbon dioxide(g) and slowly warmed to ambient temperature. The mixture was concentrated, partitioned between EtOAc and water, and the aqueous layer was washed with EtOAc (2*). The pH of the aqueous layer was adjusted (~3) by addition of 1 N HCl and then washed with EtOAc (3*). The combined extracts were dried with magnesium sulfate and concentrated. The residue was recrystallized from EtOAc yielding 200 mg (12%) of 3-chloroisonicotinic acid.

According to the analysis of related databases, 626-60-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US6610704; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1003-68-5, 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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.

5-methyl-2-pyridone (2) (20 g, 0,18 mol), K2C03 (30,4 g, 0,22 mol), NaOAc (3 g, 0,036 mol, 0,2 mol eq), CuBr (2,62 g, 0,018 mol, 0.1 mol eq) [or Cu20 (1 ,29 g, 0,05 mol eq)], Bromobenzene (4) (40,28 g, 0,26 mol, 1 ,4 mol eq) and DMSO (10 mL, 0,5 V eq) was placed in a round bottom flask under a nitrogen atmosphere. Flask was heated to 135-140C and stirred at this temperature for 6-8 h. After the completion of the reaction according to HPLC analysis, reaction medium was cooled down to about 60 C. Then, 100 mL water was added to the reaction mixture followed by 4 mL NH4OH and 100 mL toluene. The resulting mixture was stirred for 15 min and the phases were separated. Aqueous phase was extracted with 2×50 mL toluene then organic phases were combined (all extractions were carried out at about 60C). Combined organic phases were filtered over a bed of celite after treatment with charcoal. After evaporation of toluene to the dryness, 36,3 g crude pirfenidone was obtained. Crude pirfenidone purity is >99,5% (HPLC analysis, UV detector 310 nm).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; ULKAR KIMYA SANAYII VE TICARET A. S.; KOYUNCU, Hasan; AKGOL, Emre; REIS, Omer; (16 pag.)WO2016/122420; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71935-32-5, 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. 71935-32-5, name is 4-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

In toluene, 4-hydroxymethylpyridine-2-carbonitrile (111 mg, 0.83 mmol) synthesized in Production Example 87 was dissolved, and thionyl chloride (73 muL) was added thereto. The mixture was refluxed for 30 minutes. Thereafter, the mixture was allowed to cool down to a room temperature and stirred for one hour. After the completion of the reaction was confirmed by HPLC, the solvent was distilled off. The resulting residue was used for the next reaction without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71935-32-5, its application will become more common.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd; Okada, Makoto; Hasumi, Koichi; Nishimoto, Takahiro; Yoshida, Miwa; Ishitani, Kouki; Aotsuka, Tomoji; Kanazawa, Hashime; US2013/85127; (2013); A1;,
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 13602-11-4, name is Methyl 6-methylpyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 13602-11-4

Step 3 in N2 condition, compound 3 (10g, 66.2mmol), CCl4(100 ml), NBS is sequentially added in the solution (17.7g, 99 . 3mmol), AIBN (543.5 mg, 3 . 3mmol), reflux reaction 12h, after detecting reaction is complete, concentrated under reduced pressure, by adding water, extraction with ethyl acetate, combined with the phase, ethyl acetate is removed under reduced pressure, the oily compound crocatus obtained. Recrystallization with petroleum ether and ethyl acetate (10:1) finally obtaining the white solid compound 4 (7.8g), yield 51.3%. This step attempts to adopt different post-processing method, of column chromatography, recrystallization effect is not good, and recrystallization to obtain product is a white solid, no other color.

With the rapid development of chemical substances, we look forward to future research findings about 13602-11-4.

Reference:
Patent; Shanghai Institute Of Technology; Yao, Zhiyi; Zhang, Xiaopan; Zong, Haoqiang; Wang, Dongsheng; (14 pag.)CN105294552; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 104830-06-0, 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. 104830-06-0, name is 2-Amino-3-iodopyridine. A new synthetic method of this compound is introduced below.

General procedure: 2-Iodoaniline 2a (65.7 mg, 0.3 mmol), Cu(OAc)2 (6 mg, 10%), KOtBu (101 mg, 0.9 mmol), DMAc (1.0 mL) were mixed in a Schlenck tube and then to the mixture was added 2-(phenylethynyl)benzonitrile1a (74 mg, 0.36 mmol) under N2. The reaction mixture was stirred for 12 h at 120 C under N2. After the reaction was completed (monitored by TLC), the reaction mixture was then diluted with water and extracted with ethyl acetate. After the combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure, the residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to afford the pure product 3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,104830-06-0, its application will become more common.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1658-42-0, 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.1658-42-0, name is Methyl 2-(pyridin-2-yl)acetate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

Example 6 1-Adamantan-2-yl-3-cyclopropyl-4-pyridin-2-yl-1,3-dihydro-imidazol-2-one Step A1 Cyclopropylamino-pyridin-2-yl-acetic acid methyl ester; This material was obtained in analogy to example 4, step A] from alpha-bromo-pyridin-2-yl-acetic acid methyl ester (1.0 g, CAS 52458-81-8, made by bromination of pyridine-2-yl-acetic acid methyl ester according to Tetrahedron, 58, 2002, 10113-10126) and cyclopropylamine (372 mg) to cyclopropylamino-pyridin-2-yl-acetic acid methyl ester as a light yellow liquid (515 mg). MS (ESI): 206.9 (MH+).

Statistics shows that 1658-42-0 is playing an increasingly important role. we look forward to future research findings about Methyl 2-(pyridin-2-yl)acetate.

Reference:
Patent; Ackermann, Jean; Amrein, Kurt; Hunziker, Daniel; Kuhn, Bernd; Mayweg, Alexander V.; Neidhart, Werner; Takahashi, Tadakatsu; US2008/103183; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106984-91-2, 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, 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, COA of Formula: C6H5NO2, blongs to pyridine-derivatives compound. COA of Formula: C6H5NO2

Synthesis of Example 25: [Show Image] To a solution of intermediate 12e (417 mg, 1.00 mmol) in acetonitrile (20 mL) and acetic acid (200 muL) was added 6-hydroxynicotinaldehyde (123 mg, 1.00 mmol). The reaction mixture was stirred vigorously at reflux temperature overnight. The solvent was removed under reduced pressure. The crude product was purified by preparative LC-MS. The pure product (213 mg, 0.41 mmol, brown sticky solid) was dissolved in methanol (5 mL) and 1 M HCl in diethyl ether (820 muL, 0.82 mmol) was added. The solvents were removed under reduced pressure. The product was taken up in water (5 mL) and lyophilized

The synthetic route of 106984-91-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2439197; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183610-70-0, 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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

3-(trifluoromethyl)pyridin-2-amine (0.15 g, 0.92 mmol) was added to a mixture of sodium hydride (0.14 g, 5.5 mmol) and N,N-dimethylformamide (3.0 ml_) under nitrogen gas at 15 – 20 C and the reaction mixture was stirred for 15 – 20 min. Compound of example 65 (0.248 g, 1 .06 mmol) was added to the reaction mixture at 5 – 10 C and was stirred for 3 – 6 h. The reaction mixture was cooled to 10 C and methanol (0.5 ml_) was added slowly. A solution of chilled 20 % ammonium chloride solution (4.5 ml_) was added drop-wise to the reaction mixture at 10 C and was stirred for 25 – 30 min. The product was extracted in ethyl acetate (12 ml_) and the organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated to obtain the crude product, which was further purified by column chromatography to obtain the title compound. Yield: 0.07 g (21 %); 1H NMR (300 MHz, DMSO-d6): delta 9.0 (s, 1 H), 8.74 (m, 2H), 8.36 (d, 1 H), 7.80 (s, 1 H), 7.61 (m, 2H), 7.42 (m, 1 H), 7.10 (d, 1 H), 6.1 (s, 2H); MS (ES+): 361 .4 (M+1 ).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183610-70-0, 2-Amino-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SIVAKUMAR, Meenakshi; JOSHI, Kalpana, Sanjay; HARIHARAN, Sivaramakrishnan; BOKKA, Ravishankar; AWARE, Valmik, Sopan; MANOHAR, Sonal; SONAWANE, Vinay; CHENNAMSETTY, Suneelmanoharbabu; KALE, Ganesh; THOMAS, Becky, Mary; TRIVEDI, Jacqueline, Vinodkumar; WO2013/175415; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89488-29-9, 2-Bromo-4-methoxypyridine, 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, 89488-29-9, blongs to pyridine-derivatives compound. Computed Properties of C6H6BrNO

PdCI2(dppf) (0.065 g, 0.08 mmol, 0.05 eq) was added to a solution of compound 52h (0.6 g, 1.58 mmol, 1 eq), potassium acetate (0.31 g, 3.17 mmol, 2 eq) and bis(pinacolato)diboron (0.8 g, 3.17 mmol, 2 eq) in dioxane that was stirred under Ar at rt. The reaction mixture was refluxed for 16 h, cooled to rt and filtered through a plug of celite. The filter was rinsed with EtOAc and the filtrate was washed with water (20 ml) and brine (20 ml), dried over Na2S04 and concentrated. The pinacol boronate (0.7 g) thus obtained was dissolved in dioxane (25 ml). 2-bromo-4-methoxypyridine (0.265 g, 1.41 mmol), 10% aqueous K2C03 solution (3.5 ml) and finally tetrakis(triphenylphosphine)palladium(0) (0.07 g, 0.06 mmol) were added. The mixture was refluxed for 16 h, cooled to rt and filtered through a plug of celite. The filter was rinsed with EtOAc and the filtrate was washed with water (20 ml), brine (20 ml), dried over Na2S04 and concentrated. The remnant was purified by column chromatography [EtOAc/hexane = 1 :1 ]. White solid. Yield: 0.27 g. m/z: [M+H]+ = 406.8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89488-29-9, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (168 pag.)WO2017/108204; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1014613-64-9, Adding some certain compound to certain chemical reactions, such as: 1014613-64-9, name is 4-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H7BrN2, 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 1014613-64-9.

Into a 100-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (256 mg, 1.2 mmol) and N,N-dimethylformamide (5 mL). The solution was cooled to 0 C, then sodium hydride (58 mg, 1.5 mmol, 60% dispersion in mineral oil) was added portionwise. The mixture was stirred at 0 C for 30 minutes, then triisopropylsilyl chloride (0.52 mL, 2.4 mmol) was added dropwise with stirring at 0 C. The solution was stirred at room temperature overnight then quenched with water (30 mL). The mixture was extracted with ethyl acetate (3 x 30 mL), and the organics were concentrated under vacuum. The residue was purified on a silica gel column eluting with 0-5% ethyl acetate in petroleum ether to yield 4-bromo-2-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (400 mg, 90%).

According to the analysis of related databases, 1014613-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas Daniel; SKALITZKY, Donald J.; TOOGOOD, Peter L.; VANHUIS, Chad A.; (416 pag.)WO2019/200120; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem