Pyridine-derivatives

Reference of 811801-40-8, 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.811801-40-8, name is (3-((Pyridin-4-ylthio)methyl)phenyl)methanol, molecular formula is C13H13NOS, molecular weight is 231.31, as common compound, the synthetic route is as follows.

EXAMPLE 8 6,7-dichloro-2-cyclopentyl-2-methyl-5-({3-[(pyridin-4-ylthio)methyl]benzyl}oxy)indan-l-oneDitertbutylazodicarboxylate (129 mg, 0.56 mmol) was added to a stirred solution of 6,7- Dichloro^-cyclopentyl-S-hydroxy^-methylindan-l-one (500 mg, 1 mmol), {3-[(pyridin-4- ylthio)methyl]phenyl}methanol (65 mg, 0.28 mmol) and triphenylphosphine (147 mg, 0.56 mmol) in tetrahydrofuran (5 mL) at rt. The reaction mixture was stirred for 16 hr, then the solvent was removed in vacuo. The residue was purified via column chromatography on silica gel (eluting 0-80% ethyl acetate/hexanes) to give 6,7-dichloro-2-cyclopentyl-2-methyl-5-({3-[(pyridin-4- ylthio)methyl]benzyl}oxy)indan-l-one as a colorless oil. 1H NMR(CDCl3, 500MHz), ? 8.39 (d, 2H), 7.56-7.40 (m, 4H), 7.13 (d, 2H), 6.91 (s, IH), 5.23 (s, 2H), 4.26 (s, 2H), 2.97 (d, IH), 2.67 (d, IH), 2.26- 2.22 (m, IH), 1.88-1.83 (m, IH), 1.56-1.48 (m, 5H), 1.28-1.20 (m, 4H), 0.94-0.92 (m, IH). MS (ESI): 513 (M + H)+.

The chemical industry reduces the impact on the environment during synthesis 811801-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/47237; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83766-88-5, 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 83766-88-5, name is 2-(tert-Butoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

According to the analysis of related databases, 83766-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98197-72-9, 4-Iodo-2-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, Formula: C6H6INO, blongs to pyridine-derivatives compound. Formula: C6H6INO

(d) 50.6 mL of isopropyl magnesium chloride (2 mol/L tetrahydrofuran solution) was cooled with ice, and a solution having 19.8 g (84.3 mmol) of the crude product of 4-iodo-2-methoxypyridine obtained in step (c) dissolved in 80 mL of tetrahydrofuran, was added, followed by stirring at 0C for 1 hour and at room temperature for 1 hour. Then, 16.9 g (127 mmol) of N-chlorosuccinimide was gradually added, followed by stirring at room temperature for 1 hour. 100 mL of water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with ethyl ether was carried out, then the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 11.0 g (crude yield 91%) of a crude product of 4-chloro-2-methoxypyridine.1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.91(s, 3H), 6.70(d, 1H, J = 2.0 Hz), 6.81(dd, 1H, J = 6.0 Hz, 2.0 Hz), 7.99(d,1H, J = 6.0 Hz)

The synthetic route of 98197-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1559320; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1 -thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90C for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3 x 20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yield 3-[[3,3- difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; GRUNENTHAL GMBH; LUCAS, Simon; KUeHNERT, Sven; BAHRENBERG, Gregor; SCHROeDER, Wolfgang; WO2014/82737; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 902837-42-7, 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. 902837-42-7, name is 7-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

Sodium hydride (0.25 g, 6.2 mmol) is added under ice bath cooling to a mixture of 7-bromo-lH-pyrrolo[3,2-c]pyridine (0.8 g, 4.1 mmol) in DMF (10 ml). The mixture is stirred for 30 minutes before methyl iodide (0.25 ml, 4.1 mmol) is added. The mixture is warmed to RT and stirred for 17 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgS04 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 0.61 g (71%). HPLC-MS: tR=0.88 min (METHOD l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,902837-42-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; WO2015/25018; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 99368-68-0, 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, 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, 99368-68-0, blongs to pyridine-derivatives compound. Quality Control of 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

Reference Example 121 6-chloro-2-methylpyridine-3-sulfonyl chloride; Under ice-cooling, thionyl chloride (4 mL) was added dropwise to water (24 mL) over 20 min. The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, to the concentrated hydrochloric acid (6 mL) was added 5-amino-2-chloro-6-methylpyridine (1.0 g) with stirring under ice-cooling, and a solution of sodium nitrite (0.5 g) in water (2 mL) was added dropwise over 10 min. The reaction mixture was gradually added at 5 C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (10 mg). Under ice-cooling, the mixture was further stirred for 30 min, and the precipitate was collected by filtration, and washed with water to give the title compound as a pale-yellow solid (yield 1.1 g, 67%). 1H-NMR (CDCl3) delta: 2.99 (3H, s), 7.41 (1H, dd, J=8.7, 0.9 Hz), 8.26 (1H, d, J=8.4 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (2007); A1;,
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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 178876-83-0

Example 158D methyl 3-bromo-6-fluoropicolinate To a solution of nitrosonium terafluoroborate (17.8 g) in dichloromethane (100 mL) at 5 C. was added EXAMPLE 158C (26.1 g) in dichloromethane (250 mL) over 1 hour. The reaction mixture was stirred an for additional 30 minutes at 5 C., and then allowed to warm to room temperature overnight. The reaction mixture was quenched with pH 7 buffer (100 mL), and then neutralized with solid potassium carbonate. The resulting mixture was extracted with ether (twice), and the combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 1 to 10% ethyl acetate in hexanes to provide the title compound.

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, 178876-83-0, Methyl 6-amino-3-bromopicolinate.

Reference:
Patent; AbbVie Inc.; Wang, Le; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96121; (2013); A1;,
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. 327056-62-2, name is 2-Cyano-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Cyano-5-fluoropyridine

2) 2-[(5-Fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester The above 5-fluoropyridine-2-carbonitrile (11.8 g) in 6N HCl (100 mL) was refluxed for 4 hours and then cooled in air. NaCl was added to the reaction mixture to saturate the mixture, and ethyl acetate was added thereto for partitioning the mixture. The organic layer was dried over sodium sulfate anhydrate. After a filtration step, the solvent was removed under reduced pressure, and the residue was dissolved in N,N-dimethylformamide (140 mL). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.0 g), 1-hydroxybenzotriazole (770 mg), and aminomalonic acid diethyl ester hydrochloride (7.2 g) were added to the solution, and the mixture was stirred for 19.5 hours at room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate. After a filtration step, the solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane – ethyl acetate), to thereby give 2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester as a solid product (9.4 g, 53%). 1H-NMR (400MHz, CDCl3) delta:1.33 (6H, t, J=7.1Hz), 4.27-4.38(4H,m), 5.36 (1H, d, J=7.4Hz), 7.51-7.56 (1H, m), 8.20-8.21 (1H, m), 8.46 (1H, d, J=2.7Hz), 8.74 (1H, d, J=10.0Hz).

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, 327056-62-2, 2-Cyano-5-fluoropyridine.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1621537; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65147-89-9, 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.65147-89-9, name is 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine, molecular formula is C12H8BrN3, molecular weight is 274.12, as common compound, the synthetic route is as follows.

Example 223 Under an argon stream, a mixture of 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 3) (90 mg), phenylboric acid (104 mg), tetrakis(triphenylphosphine)palladium(0) (38 mg), 2 M sodium carbonate (0.82 ml) and tetrahydrofuran (3.3 ml) was stirred at 85C for 24 hours.. The mixture was distributed into ethyl acetate – tetrahydrofuran (3: 1, v/v) and water.. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure.. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate – chloroform – hexane (1: 1: 4, v/v) was concentrated under reduced pressure.. The resulting crystals were collected by filtration to obtain 2,6-diphenyl-1H-imidazo[4,5-b]pyridine (20 mg, 22 %).. The crystals were recrystallized from chloroform – methanol. HPLC (220 nm) Purity 97 % (Retention time 2.78 minutes) MS (ESI+, m/e) 272 (M+1)

Statistics shows that 65147-89-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1460067; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 195044-14-5, 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 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step-3: Synthesis of 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-tert-butyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (180 mg, 0.756 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (194.3 mg, 0.907 mmol, 1.2 eq) in 1,4 dioxane (5 mL) was added potassium carbonate (208.9 mg, 1.512 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (28.7 mg, 0.151 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (26.05 mg, 0.302 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 30% EtOAc/Hexane to afford 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 35.71%) as off white solid.

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem