Day: February 22, 2021

Synthetic Route of 105596-61-0, 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 105596-61-0, name is Ethyl 2-methoxyisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of ethyl 2-methoxy-pyridine-4-carboxylate (0.93 g, 5 mmol) in ether (5 ml) was added to lithium aluminium hydride (0.3 g, 8 mmol) in ether (10 ml) cooled to 5 C. and the mixture stirred for 2 hours. Water was added, the mixture was filtered through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-hydroxymethyl-2-methoxypyridine (0.64 g, 89%) as a yellow oil. 1 H NMR Spectrum: (CDCl3) 3.86(s, 3H); 4.62(s, 2H); 6.65(s, 1H); 6.76(d, 1H); 8.05(d, 1H) MS – ESI: 140 [MH]+

According to the analysis of related databases, 105596-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 124433-70-1, 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. 124433-70-1, name is 6-Fluoropyridine-2-sulfonamide, molecular formula is C5H5FN2O2S, 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.

6-Chloro-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxylic acid (23.7 g, 81.4 mmol) was added to a mixture of N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (35.0 g, 92.1 mmol), 6-fluoropyridine-2-sulfonamide (16.5 g, 93.8 mmol) and ethyldiisopropylamine (36 mL) in N,N-dimethylformamide (400 mL) at 5 C. The resulted mixture was stirred at room temperature overnight before it was quenched with 1 N HCl (150 mL). The mixture was diluted with water (450 mL) and the resultant solids were collected by filtration and washed with water (500 mL), methanol (200 mL) and Et2O (400 mL). The solid was purified by silica gel column chromatography (0-4% methanol/CH2Cl2) to afford 6-chloro-N-[(6-fluoro-2-pyridyl)sulfonyl]-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxamide as a white solid (22.2 g, 60%). NMR (CDCl3, 250 MHz) delta 8.36 (dd, J=15.7, 7.5 Hz, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.29 (d, J=7.8 Hz, 1H), 6.91 (s, 2H), 2.25 (s, 3H), 1.94 (s, 6H).

According to the analysis of related databases, 124433-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86649-57-2, Adding some certain compound to certain chemical reactions, such as: 86649-57-2, name is 3-Pyridyloxyacetic acid,molecular formula is C7H7NO3, 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 86649-57-2.

Add slowly 1-propanephosphonic acid cyclic anhydride (122.30 g, 100.00 mL,192.18 mmol) to a solution of 2-hydroxy-2-methyl-N-( 1,2,3 ,4-tetrahydroisoquinolin-6-yl)propane-1-sulfonamide hydrochloride (46.90 g, 146.18 mmol), 2-(3-pyridyloxy)acetic acid (27.00 g, 176.31 mmol), dimethylformamide (708.98 g, 750.00 mL, 9.70 mol), triethylamine (59.53 g, 82.00 mL, 588.31 mmol) at 0 C. Allow the reaction to warm slowly to room temperature and stir overnight. Add saturated aqueous sodium sulfate solution (500 mL) and water (500 mL). Extract with dichloromethane (3 xl L), combine the organic layers, dry over anhydrous sodium sulfate, filter and concentrate underreduced pressure. Purify by silica gel chromatography eluting with a mobile phase of dichloromethane/methanol (0% to 10% methanol over 90 minutes). Combine fractions containing a mixture of peaks from previous purification and purify by silica gel chromatography eluting with a mobile phase of dichloromethane/methanol (0% to 10% methanol over 45 minutes) to afford the title compound (8.00 g, 19.05 mmol).Combine the two fractions to afford the title compound (38.00 g, 90.58 mmol). MS (m/z): 420 (M+1).

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. 86649-57-2, 3-Pyridyloxyacetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; BURKHOLDER, Timothy Paul; DEL PRADO, Miriam Filadelfa; FERNANDEZ, Maria Carmen; HEINZ II, Lawrence Joseph; PRIETO, Lourdes; ZHAO, Genshi; WO2015/54060; (2015); 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. 1222185-12-7, name is Dimethyl 3-bromopyridine-2,4-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Dimethyl 3-bromopyridine-2,4-dicarboxylate

Dimethyl 3-phenylpyridine-2,4-dicarboxylate Z3’A stirred suspension of 3-bromopyridine 11 (300 mg, 1.1 mmol, 1 eq.), phenyl boronic acid/anhydride (147 mg, 1.2 mmol, 1.1 eq.), Cs2CO3 (392 mg, 1.2 mmol, 1.1 eq.), Pd(OAc)2 (25 mg, 0.11 mmol, 0.1 eq.) and PPh3 (57 mg, 0.22 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 C for 3 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers were washed with water, dried(Na2SO4) and concentrated in vacuo. The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EtOAc/hexane) to affordZ3′ (223 mg, 75%) as a light yellow oil.1H NMR deltaH (400 MHz; CDCl3) 3.61 (s, 3H, OCH3), 3.68 (s, 3Eta, OCH3), 7.23 (dd, J=6.5, 3.0 Hz, 2H, ArHmeta), 7.39 (m, 3Eta, ArH), 7.73 (d, J=5.0 Hz, IH, pyHmeta), 8.76 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.6 (CH3), 52.6 (CH3), 124.2 (ArCH), 128.0 (ArCH), 128.2 (ArCH), 128.4 (ArCH), 135.2 (ArQ, 135.7 (ArQ, 140.5 (ArQ, 148.6 (ArCH), 150.8 (ArQ, 166.4 (CO), 166.5 (CO); IR vmax (filmycm 1 3059, 3027, 3003, 2952, 1740, 1434, 1320, 1288, 1199; HRMS (ESI+) for C15H13NNaO4 requires 294.0737, found (M+Na+) 294.0730; 3-PhenyIpyridine-2,4-dicarboxylic acid Z31H NMR deltaH (400 MHz; MeOD) 7.26-7.36 (m, 2H, ArH), 7.38-7.42 (m, 3Eta, ArH), 7.80 (d, J=5.0 Etaz, IH, pyHmeta), 8.69 (d, J=5.0 Etaz, IH, pyHortho); 13C NMR deltac (100 MHz, DMSO-J6) 123.6 (ArCH), 128.8 and 128.9 (2 x ArCH), 129.6 (ArCH), 132.3 (AiQ, 136.4 (ArQ, 142.8 (ArC), 149.2 (ArCH), 153.6 (ArQ, 168.4 (CO), 168.5 (CO); IR Vn^ (KBr diskycm”1 3424, 2920, 2852, 1729, 1612, 1379, 1259, 1192; HRMS (ESI-) for C13H8NO4 requires 242.0459, found (M-H”) 242.0453;

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, 1222185-12-7, Dimethyl 3-bromopyridine-2,4-dicarboxylate.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
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. 74115-12-1, name is 5-Chloro-3-hydroxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4ClNO

EXAMPLE 3 Synthesis of 5-Chloro-3-pyridinyl trifluoromethanesulfonate Trifluoromethanesulfonic anhydride (5.0 mL, 30 mmol) was dissolved in CH2Cl2 (100 mL), and cooled to 0 C. 5-Chloro-3-pyridinol (3.10 g, 23.9 mmol), and triethylamine (6.5 mL, 47 mmol) were dissolved in CH2Cl2 (50 mL), and the resulting solution was added to the cold trifluoromethanesulfonic anhydride solution dropwise via cannula. The resulting dark brownish-red solution was stirred at 0 C. for 5 minutes, and then the ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After stirring for 16 h at ambient temperature the reaction was quenched by pouring into water and basified by addition of saturated aqueous sodium carbonate. The basic aqueous phase was extracted with CH2Cl2 (2*50 mL), the combined organics dried over Na2SO4, filtered and concentrated in vacuo. The resulting black viscous oil was filtered through a plug of silica gel and fractions were collected while eluding with 1:1 hexane:ethyl acetate. Fractions containing the desired product were combined, concentrated in vacuo, and further purified by column chromatography eluding with 15:1 then 10:1 hexane:ethyl acetate to afford 5-chloro-3-pyridinyl trifluoromethanesulfonate (3.68 g, 59% yield) as a golden liquid. 1H NMR (CDCl3, 300 MHz) Delta8.65 (d, J=2 Hz, 1H), 8.52 (d, J=2 Hz, 1H), 7.70 (t, J=3 Hz, 1H). MS (ESI) 261 (M+, 35Cl), 263 (M+, 37Cl).

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, 74115-12-1, 5-Chloro-3-hydroxypyridine.

Reference:
Patent; Cosford, Nicholas D.; Roppe, Jeffrey R.; Tehrani, Lida R.; Smith, Nicholas D.; Stearns, Brian; Huang, Dehua; Wang, Bowei; US2005/43307; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 766-16-5, 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 766-16-5, name is 4-Fluoro-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of l-cyclopropyl-6-(lH-imidazol-4-yl)-3,3-dimethyl-lH-pyrrolo[3,2-c]pyridin- 2(3H)-one (80 mg), 4-fluoro-2-methylpyridine (42 mg) and cesium carbonate (185 mg) in acetonitrile (1 ml) was heated to reflux temperature for 3 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, 0% to 10% MeOH in dichloromethane) to give the title compound (59 mg, 55%) as a white foam. MS (ESI, m/z): 360.3 [(M+H)+].

According to the analysis of related databases, 766-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); 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. 75711-00-1, name is 2-Chloro-3-methoxy-5-nitropyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-3-methoxy-5-nitropyridine

Step 1: 2,3-Dimethoxy-5-nitropyridine A round bottom flask was charged with methanol under nitrogen. Freshly cut sodium (91 mg, 3977 mumol) was added, and the mixture was stirred at RT under nitrogen until the sodium had dissolved. 2-Chloro-3-methoxy-5-nitropyridine (500 mg, 2652 mumol) was added and the reaction mixture was stirred under nitrogen at RT. After ?15 min the mixture became heterogeneous and thick, and GC/MS analysis of a sample taken at 0.5 h indicated complete conversion to the desired product. The mixture was diluted with DCM and water and the layers were separated. The aqueous portion was extracted with additional DCM and the combined organics were dried, filtered and concentrated. The crude solid was passed through a silica plug using 5% MeOH/DCM. The filtrate was concentrated to provide 2,3-dimethoxy-5-nitropyridine as a light yellow solid. MS [M+H]=185.

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, 75711-00-1, 2-Chloro-3-methoxy-5-nitropyridine.

Reference:
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52833-94-0, 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 52833-94-0 as follows.

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4C1 (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentratedin vacuo, suspended in water and extracted with CH2C12. The organic layer was washed with brine,dried over Na2504 and concentrated to give the product of 2-amino-5-bromonicotinamide (1.80 g,yield: 80%), which was used for the next step without further purification. ?H NMR (DMSO-d6,400 MHz) 8.14 (dd, J= 4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H):216/218.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52833-94-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); 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 1186647-69-7, name is 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1186647-69-7

A suspension of 4-chloro-3-iodo-1H-pyrozolo[4,3-c]pyridine (7.88 g, 0.0280 mol) in DCM (100 mL) was stirred at 0 C. for 5 minutes. TEA (5.62 g, 0.0560 mol) was added and the mixture was stirred for 10 minutes. Trityl chloride (11.7 g, 0.0420 mol) was then added. After being stirred for 3 hours, the reaction mixture was treated with water (100 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as an off-white solid (13.2 g, 89%).

With the rapid development of chemical substances, we look forward to future research findings about 1186647-69-7.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Estrada, Anthony; Shore, Daniel; Sweeney, Zachary; US2014/288043; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 82205-58-1, 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. 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine, molecular formula is C9H12N4O2, 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 acetylation/sulphonylation procedure). Compound 3b (208 mg, 1 mmol), acetyl chloride (79 mul, 1.1 mmol) and PS-NMM (100 mg) in CH2Cl2 (5 mL) were stirred for 16 h. After adding PS-Trisamine (150 mg) to the reaction mixture was left to stir for a further 2 h, filtered and concentrated in vacuum to afford a yellow solid: 250 mg (90%) yield. 1H NMR CDCl3 delta = 9.03 (1H, d, J = 2.5 Hz), 8.23 (1H, dd, J1, J2 = 2.9 Hz), 6.59 (1H, d, J = 9.5 Hz), 3.89-3.58 (8H, m), 2.13 (3H, s). 13C NMR CDCl3 delta = 169.4, 160.2, 146.2, 135.5, 133.2, 104.7, 44.7 (2C), 44.3 (2C), 21.4. IR (neat, cm-1): 1643, 1596, 1512, 1424, 1340, 1299, 929. HRMS m/z calculated for C11H15N4O3 (MH+): 251.1139, Found: 251.1140.

According to the analysis of related databases, 82205-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spencer, John; Patel, Hiren; Callear, Samantha K.; Coles, Simon J.; Deadman, John J.; Tetrahedron Letters; vol. 52; 45; (2011); p. 5905 – 5909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem