Pyridine-derivatives

Electric Literature of 824429-51-8, Adding some certain compound to certain chemical reactions, such as: 824429-51-8, name is tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate,molecular formula is C11H16N2O3, 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 824429-51-8.

N- [2- (hydroxymethyl) pyridin-3-yl] carbamic acid tert-butyl ester(0.15 g) in dichloromethane (1 mL)Thionyl chloride (0.096 g) was added, and the mixture was stirred at room temperature for 1 hour.The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and the crude product was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (chloromethyl) pyridin-3-yl] carbamic acid tert-butyl ester (0.12 g).A mixture of the product (0.12 g), dichloromethane (2 mL), potassium cyanide (0.039 g), tetrabutylammonium hydrogen sulfate (0.017 g) and water (0.5 mL) was stirred at room temperature for 3 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the crude product was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (cyanomethyl) pyridin-3-yl] carbamic acid tert-butyl ester.Concentrated hydrochloric acid (0.072 g) and 10% palladium on carbon (50% wet, 0.03 g) were added to the product methanol (3 mL) – dichloromethane (3 mL) mixture, and the mixture was stirred at room temperature under a hydrogen atmosphere (0.32 MPa) Followed by stirring. The reaction mixture was passed through a celite pad and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: ethyl acetate / methanol) to give the title compound (0.011 g). Structural formula, spectral data and purification conditions are shown in Table 26.

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. 824429-51-8, tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Hirasawa, Hideaki; Tanada, Fumiya; Mutai, Yousuke; Fushimi, Nobuhiko; Kobayashi, Junichi; Kijima, Yoshiro; (267 pag.)JP2018/108988; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98198-48-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 98198-48-2 as follows.

A mixture of 2-amino-5-bromo-4-methylpyridine (2.0 g, 10.7 mmol) and CuCN (1.1 g, 12.3 mmol) in DMF (2.5 mL) wasrefluxed for 4 h. After the mixture was cooled to room temperature, NaCN (2.15 g) and H2O (6.5mL) were added, and the mixture was stirred and extracted by AcOEt. The solution was washedby aq. 10% CuCN and brine. After the solvent was removed under vacuo, the residue waschromatographed on silica gel (AcOEt/hexane = 1 : 1) to give 2-amino-5-cyano-4-methylpyridine (829 mg, 58%). A solution of 2-amino-5-cyano-4-methylpyridine (706 mg, 5.3mmol) in EtOH (8.8 mL) and aq. 10N NaOH (8.8 mL) was refluxed for 24 h. After cooled toroom temperature, the mixture was diluted by adding H2O (35 mL), neutralized by aq. HCl, and filtered. The solid was washed by ether and H2O to give 6-amino-4-methylpicolinic acidcontaining NaCl (879 mg), which was dissolved in MeOH (16 mL). To this mixture was addedSOCl2 (0.7 mL, 6.7 mmol) and the mixture was refluxed for 20 h. After cooled to roomtemperature, the solvent was removed under vacuo. To the residue H2O (20 mL) was added andpH was adjusted to 13 by aq. 1N NaOH and filtered. The solid was washed by H2O and driedunder vacuo to give 2-amino-5-methoxycarbonyl-4-methylpyridine (484 mg), which wasdissolved in aq 15% H2SO4 (10.4 mL). To the solution was added NaNO2 (402 mg, 5.81 mmol)at 0 C and the mixture was stirred for 2 h at 0 C and, then, 2 h at room temperature. Themixture was extracted by AcOEt and the solvent was removed under vacuo. The residue waschromatographed on silica gel (AcOEt) to give 2bd (105 mg, 21%):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98198-48-2, its application will become more common.

Reference:
Article; Yamaguchi, Ryohei; Kobayashi, Daiki; Shimizu, Mineyuki; Fujita, Ken-ichi; Journal of Organometallic Chemistry; vol. 843; (2017); p. 14 – 19;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63897-12-1, 2,4-Dichloro-6-methyl-3-nitropyridine, 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, 63897-12-1, blongs to pyridine-derivatives compound. Safety of 2,4-Dichloro-6-methyl-3-nitropyridine

EXAMPLE 1022-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-6-methyl-1 -[2-(methyloxy)ethyl]-4-(4- mor holinyl)-1 H-imidazo[4,5-c]pyridineStep 1 . 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4-pyridinamineTo a solution of 2,4-dichloro-6-methyl-3-nitropyridine (1 g, 4.83 mmol) and triethylamine (0.741 ml, 5.31 mmol) in Nu,Nu-Dimethylformamide (DMF) (1.959 ml) at 0 C was added a solution of 2-methoxyethlyamine (0.424 ml, 4.88 mmol) in Nu,Nu-Dimethylformamide (DMF) (0.535 ml). Removed from ice bath and stirred at rt overnight. LCMS showed mainly desired product along with a small amount of the undesired regioisomer as well as the bis addition product. Quenched with water and diluted with Et20. Separated and extracted twice more with Et20. Washed combined organics with water twice, then with brine, dried on MgS04, filtered and concentrated. Purified via Biotage FCC (0-20% EtOAc / hex) Desired and bis-addition product co-eluted. Combined all product-containing fractions and concentrated resulting in a bright yellow solid. Suspended in hexanes, sonicating to break up large particles. Sonicated for 20 min. Filtered and collected bright yellow solid that was pure desired product: 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4- pyridinamine (466 mg, 1.897 mmol, 39.3 % yield). MS (m/z): 246.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63897-12-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BODMER, Vera, Q.; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; KING, Bryan, W.; LAKDAWALA SHAH, Ami; LEISTER, Lara, Kathryn; WANG, Gren, Z.; WISNOSKI, David, Duff; HARRIS, Philip, A.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; WILSON, Matthew, A.; WO2011/123609; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-36-4, 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. 884494-36-4, name is 3-Bromo-2-chloro-5-fluoropyridine, molecular formula is C5H2BrClFN, 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.

To a solution of urea compound with hydrogen peroxide (1 : 1) (1.34, 14.3 mole) and trifluoroacetic anhydride (2 mL, 14.3 mole) in 10 mL dichloromethane at 0 C for at least 15 minutes was added 3- fluoro-5-bromopicolinonitrile (500 mg, 2.38 mmol). The reaction mixture was stirred at 40 C for 2 hours. The reaction quenched with saturated aqueous NaHC03 (20 mL) and then extracted with DCM (20 mL x 5). The combined organics were dried over anhydrous Na2SC”4 and concentrated to give the crude title compound, which was carried forward without purification. MS: 226, 228 (M+l).

According to the analysis of related databases, 884494-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 851386-31-7, 2,3-Difluoroisonicotinic acid, 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, 851386-31-7, blongs to pyridine-derivatives compound. Product Details of 851386-31-7

2,2,2-trifluoroacetic anhydride (7.97 g, 37.9 mmol) was added to a stirred mixture of 2,3-difluoroisonicotinamide (3.00 g, 19.0 mmol), and triethylamine (5.76 g, 56.9 mmol) in DCM (30 mL) at15 C, and the resulting mixture was stirred at 15 C for 17 h. The mixture was diluted with H20 (50 mL). The water layer was extracted with DCM (40 mLx3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by Si02 column chromatography (heptane: EtOAc = 95:5 to 40:60) to give 2,3- difluoroisonicotinonitrile as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851386-31-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; FRALEY, Mark, E.; JONES, Kristen, G.; (139 pag.)WO2017/222952; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121912-29-6, 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. 121912-29-6, name is Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Step 2: Synthesis of 1-(4-pyridyl)-4-piperidinecarboxylic acid hydrochloride: 2.95 g (12.6 mmol) of ethyl 1-(4-pyridyl)-piperidine-4-carboxylate was stirred in 100 ml of dioxane. After adding 50 ml of 1 N hydrochloric acid, the obtained mixture was stirred at 95C for 20 hours. The solventwas evaporated under reduced pressure to obtain the title compound. Yield: 3.21 g (11.5 mmol) (91 %) MS (ESI, m/z) 207 (MH+) H-NMR (DMSO-d6) delta 1.54 (2H, t), 1.90 (2H, d), 2.60-2.70 (1H, m), 3.30 (2H, t), 4.10 (2H, d), 7.19 (2H, d), 8.20 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,121912-29-6, Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Ajinomoto Co., Inc.; EP1065200; (2001); 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. 13194-60-0, name is 3-Chloro-4-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C5H3ClN2O2

3-chloro-4-nitropyridine (5 g, 31.63 mmol), 3-pyridineboronic acid (3 g, 37.75 mmol) was added to a 500 ml single-necked flask.50 ml of a 2 M potassium carbonate aqueous solution was dissolved in a solvent of 50 ml of ethanol and 100 ml of toluene.Under the protection of N2, PdCl2(PPh3)2 (0.75 g, 0.98 mmol) was added. The temperature was slowly raised to 100 C, and the mixture was reacted under reflux for 24 hours.After cooling, the layers were separated, and the organic layer was evaporated, and then, with petroleum ether and ethyl acetate (1.5:1).4.5 g of a pale yellow solid were obtained in a yield of 60%.

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, 13194-60-0, 3-Chloro-4-nitropyridine.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ye Shaofeng; (96 pag.)CN109422743; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54189-82-1, 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. 54189-82-1, name is 6-Chloro-N-methylnicotinamide, molecular formula is C7H7ClN2O, 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.

Example 101 Preparation of N-Methyl-6-(1-oxo-2-(2-(pyrrolidin-1-yl)ethyl)-1,2,3,4-tetrahydro-isoquinolin-6-yloxy)nicotinamide hydrochloride A suspension of NaH (60% dispersion in mineral oil, 0.06 g, 5.4 mmol) in DMF at room temperature was treated dropwise over a 15 min period with a solution of 6-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroisoquinolin-1(2H)-one (0.2 g, 2.7 mmol) in DMF, stirred at room temperature for 30 min, treated with a solution of 6-chloro-n-methylnicotinamide in DMF, heated at 100 C. overnight, cooled to room temperature, diluted with water and extracted with CH2Cl2. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by ISCO CombiFlash chromatography (silica, 0-15% methanol in methylene plus 0.5% ammonium hydroxide) to afford the free amine of the title product as a colorless oil. The oil was dissolved in ethanol, treated with ethereal HCl, stirred and filtered. The filtercake was washed with ether and dried to provide the title compound as a white solid, 30 mg (10%), mp 228-230 C.; identified by NMR and mass spectral analyses. MS (ES) m/z 395.2 [M+H]+.

According to the analysis of related databases, 54189-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/69300; (2009); 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. 18438-38-5, name is 2-(Methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

EXAMPLE 7 An aqueous solution consisting of (i) 522.7 g (1.2 mol) of a 27% sodium hypobromite aqueous solution prepared by instilling bromine into a 30% sodium hydroxide aqueous solution and (ii) 8.4 g (0.2 mol) of 95% sodium hydroxide was cooled to 0 C. The 23.8 g of 2-(methylthio)pyridine obtained in Example 6 was instilled into this aqueous solution over 3 hours while keeping the temperature at 0 to 5 C., and stirring was then carried out for 7 hours at 0 to 5 C. The reaction product, which precipitated out as crystals, was filtered, washed with water, and dried, thus obtaining 71.1 g of 2-(tribromomethylsulfonyl)pyridine (purity 99%). The yield relative to the 2-(methylthio)pyridine was 95.0%. The melting point of the 2-(tribromomethylsulfonyl)pyridine obtained was 160 to 161 C.

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, 18438-38-5, 2-(Methylthio)pyridine.

Reference:
Patent; Sumitomo Seika Chemicals Co., Ltd.; US6420564; (2002); B1;,
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. 6311-35-9, name is 6-Bromonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinic acid

EXAMPLE 31 2-bromo-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine The desired product was prepared by substituting 6-bromonicotinic acid for 2-methylnicotinic acid in Example 1. After workup the crude compound was purified by HPLC on C-18 column using a solvent system increasing over 50 minutes in a gradient of 5% to 100% acetonitrile/water containing 0.01% TFA to provide the desired product as the trifluoroacetate salt. MS m/e 268.9 (M+H)+; 1H NMR (DMSO-d6) delta0.86 (d, 0.75H), 1.25 (d, 2.25H), 1.48-1.63 (m, 1H), 1.66-1.80 (m, 1H), 1.81-1.97 (m, 1H), 2.00-2.13 (m, 1H), 3.27-3.37 (m, 0.5H), 3.45-3.54 (m, 1.5H), 3.88-4.00 (m, 0.25H), 4.09-4.21 (m, 0.75H), 7.72 (d, 1H), 7.87 (dd, 1H), 8.52 (d, 1H).

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, 6311-35-9, 6-Bromonicotinic acid.

Reference:
Patent; Haviv, Fortuna; Brandley, Michael F.; Henkin, Jack; US2003/195192; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem