Category: pyridine-derivatives

Electric Literature of 71255-09-9, 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. 71255-09-9, name is 2-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

A 1.8 M THF solution of LDA (0.45 mL, 0.81 mmol) was added to a -78 C THF solution (3 mL) of [2-(3-cyano-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-bis-carbamic acid tert-butyl ester (310 mg, 0.68 mmol). After 3 min a THF solution (1 mL) of 2-methoxy-pyridine-3- carbaldehyde (0.09 mL, 0.81 mmol) was added and the reaction was warmed to room temperature. Saturated aqueous ammonium chloride was added and the crude reaction mixture was extracted with ethyl acetate. The combined extracts were dried (Na2SO4), concentrated and purified via column chromatography to give 130 mg of the title compound. 1H NMR (300 MHz, CHLOROFORM-d) delta 8.70 (t, J= 1.41 Hz, 1H), 8.63 (dt, J= 1.48, 7.96 Hz, 1H), 8.09 (dd, J = 1.79, 4.99 Hz, 1H), 7.62 – 7.70 (m, 2H), 7.46 – 7.54 (m, J = 8.10 Hz, 1H), 7.45 (d, J= 1.13 Hz, 1H), 7.33 (br. s., 1H), 6.89 (dd, J= 4.90, 7.35 Hz, 1H), 6.18 (d, J = 6.03 Hz, 1H), 3.95 (s, 3H), 3.36 (d, J= 6.03 Hz, 1H), 1.49 (s, 9H); 490 (M+H).

According to the analysis of related databases, 71255-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, J., Kent; LEONARD, Kristi; CHAKRAVARTY, Devraj; SHOOK, Brian, Christopher; WANG, Aihua; WO2010/45012; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10366-35-5, 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. 10366-35-5, name is 2-Chloronicotinamide, molecular formula is C6H5ClN2O, 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.

General procedure: A microwave reaction tube was charged with an amide (1 equiv.), PdCl2(MeCN)2 (5 mol%) and BINAP (5 mol%), The tube was evacuated and backfilled with argon (3 times), and then dry DMF (4 mL/1 mmol of starting material), phenylacetylene (1.5 equiv.), and DBU (2 equiv.) were added. The mixture was sparged with argon for 5 min and then irradiated under microwaves at 120 C for 30 minutes. After cooling to room temperature, the solvent was partially removed in vacuo, then the mixture was diluted in EtOAc (10 mL), washed with water (5 mL) and brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated. The crude product was purified by chromatography on silica gel to give the desired product.

According to the analysis of related databases, 10366-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hellal, Malik; Cuny, Gregory D.; Tetrahedron Letters; vol. 52; 42; (2011); p. 5508 – 5511;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52605-98-8, 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.52605-98-8, name is 5-Bromo-2,3-dimethoxypyridine, molecular formula is C7H8BrNO2, molecular weight is 218.05, as common compound, the synthetic route is as follows.

5,6-Dimethoxynicotinaldehyde (42) To a solution of 5-bromo-2,3-dimethoxypyridine (41, 21.7 g, 99.5 mmol) in anhydrous tetrahydrofuran (200 mL) was dropwise added n-butyl lithium (48.0 mL, 2.5 mol/L in hexane) at -78 C. under N2. The mixture was stirred for at -78 C. for 1 h. Then N, N-dimethylformamide (16.2 mL) was added to the mixture at -78 C. The reaction mixture was stirred for another 30 min at -78 C. After the reaction was completed, the mixture was quenched by saturated NH4Cl(sat.), extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo. The residue was purified by flash chromatogram with ethyl acetate/petroleum ether (1:3) to afford 5,6-dimethoxynicotinaldehyde (42) as a yellow solid (13.5 g, 81%). ESI-MS, m/z=168 [M+H]+.

Statistics shows that 52605-98-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,3-dimethoxypyridine.

Reference:
Patent; Tsai, Guochuan Emil; Wang, Ching-Cheng; Hsieh, Yuan-Ting; (53 pag.)US2019/112289; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7379-35-3, name is 4-Chloropyridine hydrochloride, the common compound, a new synthetic route is introduced below. Formula: C5H5Cl2N

Amine F-11: 2-(1-(Pyridin-4-yl)piperidin-4-yl)ethanamine dihydrochioride(i): Tert-butyl 2-(piperidin-4-yl)ethylcarbamate (0.2 g, 0.876 mmol), 4-chloro-pyridinium chloride (0.197 g, 1.314 mmol) and N-ethyl-diisopropylamine (0.37 ml, 2.19 mmol) were refluxed for 15 hours in 2-propanol (10 ml). Saturated sodium hydrogen carbonate solution (20 ml) and ethyl acetate (50 ml) were added, the phases were separated, and the aqueous phase was extracted with ethyl acetate (2.x.50 ml). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/methanol/ammonia (25percent aq.), 400:100:50:1). Yield: 80 mg (30percent).

The synthetic route of 7379-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUENENTHAL GmbH; US2010/173889; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 626-64-2, name is Pyridin-4-ol, the common compound, a new synthetic route is introduced below. SDS of cas: 626-64-2

General procedure: To a mixture of chlorinated derivatives of dihydropyrimidinonederivatives 4a-i (1 equiv.), potassium carbonate (2.5 equiv.) in acetonitrile,under 80 C was added different aryl/ heteroaryl alcohols(5a-k, 0.75 equiv.) and stirred under reflux till complete consumptionof the starting materials as determined by TLC. The solvent was thenremoved using rotary evaporator and extracted using ethyl acetate(25 mL×3) and water. The organic layer was concentrated under invacuo and the residue obtained was chromatographed on silica gel(elution with hexane/EtOAc=7:3-5:5) to provide the 2-oxo-6-(aryloxymethyl)-4-aryl/heteroaryl-1,2,3,4-tetrahydropyrimidine-5-carboxylatederivatives 6a-s in moderate to good yields.

The synthetic route of 626-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sana, Sravani; Tokala, Ramya; Bajaj, Deepti Madanlal; Nagesh, Narayana; Bokara, Kiran Kumar; Kiranmai, Gaddam; Lakshmi, Uppu Jaya; Vadlamani, Swapna; Talla, Venu; Shankaraiah, Nagula; Bioorganic Chemistry; vol. 93; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 143468-13-7, Adding some certain compound to certain chemical reactions, such as: 143468-13-7, name is 6-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 143468-13-7.

General procedure: The appropriate heterocycle (1 equiv.) was dissolved in a mixture of DMF and THF (1:1 or 1:1.5 respectively, 0.2 M). The solution was cooled to 0 C and sodium hydride (1.2 or 2.2 equiv.) carefully added portion wise. After approximately 5 min the alkyl halide (1.2 equiv.) was carefully added portion-wise. The reaction mixture was stirred at 0 C or at RT for 15 min. to an hour then heated at 80 C for a period ranging between 30 min to 6 h. The reaction mixture was cooled to 0 C and quenched with water and treated with EtOAc and the organic layer separated. The organic solvent was dried (using either MgSO4, Na2SO4 or a phase separator) and subsequently removed under vacuum. The residue was purified by flash silica column chromatography or reverse phase column chromatography to give the product.

According to the analysis of related databases, 143468-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB Biopharma SPRL; The designation of the inventor has not yet been filed; (80 pag.)EP3527209; (2019); 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.1186647-69-7, name is 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H3ClIN3, molecular weight is 279.47, as common compound, the synthetic route is as follows.HPLC of Formula: C6H3ClIN3

A mixture of 4-Chloro-3-iodo-lH-pyrazolo[4,3-c]pyridine (570.0 mg, 2.05 mmol, 1.0 eq), 3-chloro-6- (chloromethyl)quinoline (522.0 mg, 2.46 mmol, 1.2 eq) and KOH (230.0 mg, 4.1 mmol, 2.0 eq) in DMF (10.0 mL) was stirred at rt overnight. 30.0 mL of H20 was added and the mixture wasextracted with EA (15.0 mL X 3). The combined organic layers were washed with brine (15.0 mL X 3), dried over anhydrous Na2S04, then concentrated in vacuo. The resulting residue was purified by column chromatography to provide 3-chloro-6-((4- chloro-3-iodo-lH-pyrazolo[4,3-c]pyridin-l-yl)methyl)-7,8-dihydroquinoline (380 mg, 41%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1186647-69-7, 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 21642-98-8, Adding some certain compound to certain chemical reactions, such as: 21642-98-8, name is 4-Methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C7H6N2O2, 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 21642-98-8.

2,4-dichloronicotinonitrile A solution of 5.0 g of commercial 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile in 50 ml of phosphorus oxychloride is refluxed for 19 hours. After cooling, the reaction medium is poured into a mixture of water and ice. The precipitate formed is filtered off and the filtrate is extracted twice with a 90/10 ethyl acetate/methanol solution. The combined organic phases and the precipitate are dried over magnesium sulfate and then concentrated under reduced pressure to give 6.76 g of a yellowish powder. The crude product is purified on a prepacked Biotage KP-Sil column of 60 A SiO2 32-63 muM (5/95 to 10/90 gradient ethyl acetate in cyclohexane) to give 2.08 g of a white powder of 2,4-dichloronicotinonitrile. MS-IE: 172=[M+] (base peak), 137=[M+]-Cl IR spectrum (KBr): 3072; 2236; 1559; 1539; 1445; 1368; 1220; 1197; 1069; 859; 818; 791 and 416 cm-1 1H NMR spectrum (400 MHz, (CD3)2SO, delta in ppm): 7.92 (d, J=5.5 Hz, 1H); 8.67 (d, J=5.5 Hz, 1H)

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. 21642-98-8, 4-Methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2008/39491; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55676-22-7, 3-Acetyl-6-chloropyridine, 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, 55676-22-7, blongs to pyridine-derivatives compound. HPLC of Formula: C7H6ClNO

To a stirring solution of 1-(6-chloro-pyridin-3-yl)-ethanone (l.Ommol, CAS No. 55676-22-7) and 4-methoxycarbonylphenyl boronic acid (1.2mmol) in dioxane (0.15M), add tetrakis- (triphenylphosphine) (0.044mmol) and 2M aqueous sodium carbonate (5.0mmol). Heat the reaction to 90C for three hours. After this time, remove the heat and concentrate in vacuo. Purify the title compound via radial chromatography eluting with methanol and dichloromethane. MS (m/e): 256.1 (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55676-22-7, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97740; (2005); 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. 186593-43-1, name is 5-Amino-3-bromo-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H7BrN2

[0196] A stirred mixture of 5-bromo-6-methylpyridin-3-amine (0.100 g, 0.535 mmol), 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?jbi[[1 ,3,2] dioxaborolanyll (0.136 g, 0.535 mmol), [1,1 bis(diphenylphosphino)ferrocenej dichloropalladium(II) complexed with dichloromethane (1:1) (42 mg, 0.051 mmol) and potassium acetate (0.150 g, 1.53 mmol) in 1,4-dioxane (5.0 mL) was heated at 110C. After 2 hours, the reaction was quenched with saturated aqueous NH4C1, and extracted with DCM (3 x30 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The crude product was used directly in the next step without further purification.

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, 186593-43-1, 5-Amino-3-bromo-2-methylpyridine.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; SHEN, Bo; YAO, Wenqing; (114 pag.)WO2016/134294; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem