Month: February 2021

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.7379-35-3, name is 4-Chloropyridine hydrochloride, molecular formula is C5H5Cl2N, molecular weight is 150.0059, as common compound, the synthetic route is as follows.Quality Control of 4-Chloropyridine hydrochloride

Step 1.Methyl(4-nitrophenyl)-4-pyridylamine To a suspension of N-methyl-4-nitroaniline (2.0 g, 13.2 mmol) and K2CO3 (7.2 g, 52.2 mmol) in DMPU (30 mL) was added 4-chloropyridine hydrochloride (2.36 g, 15.77 mmol).The reaction mixture was heated at 90¡ã C. for 20 h, then cooled to room temperature.The resulting mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL).The organic layer was washed with water (100 mL), dried (Na2SO4) and concentrated under reduced pressure.The residue was purified by column chromatography (silica gel, gradient from 80percent EtOAc/20percent hexanes to 100percent EtOAc) to afford methyl(4-nitrophenyl)-4-pyridylamine (0.42 g)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7379-35-3, 4-Chloropyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Paulsen, Holger; Riedl, Bernd; Scott, William J.; Smith, Roger A.; Wood, Jill; Hatoum-Mokdad, Holia; Lee, Wendy; Redman, Aniko; Johnson, Jeffrey; Sibley, Robert; US2012/46290; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 677728-92-6, 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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde, molecular formula is C6H4FNO, 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.

Dissolve 2-fluoro-5-formyl pyridine (5.70g, 45.6mmol) in THF (lOOmL) and cool to -78C. Slowly add via cannula, a solution of 3-butenylmagnesium bromide (lOOmL, SOmmol) over 20mm. Stir the resulting mixture at -78C for 45mm, then warm to 0C and stir for 2h, then allow mixture to warm to room temperature over lh. Slowly addsaturated aq. solution of NaHCO3 (1 OOmL) and pour the mixture into water (1 OOmL). Extract the mixture with diethyl ether (3 X lOOmL) and combine the organic solutions. Wash the organic solution with water (2 X 1 OOmL) and brine (1 OOmL), then dry over Na2504, filter and concentrate in vacuo. Purify the crude oil by flash chromatography, using a linear gradient of 100% hexanes to 80% EtOAc/hexanes as eluant, to give the titlecompound (5.16g, 62%) as a clear colorless oil. MS [EI+] 182.0 (M+H). ?H NMR(400MHz, CDC13): 8.12 (m, 1H), 7.88 (dt, 1H, J 2.5, 8.3), 7.09 (dd, 1H, J 2.8, 8.5),5.78 (m, 1H), 5.38 (d, 1H, J 4.6), 4.96 (m, 1H), 4.90 (m, 1H), 4.78 (m, 1H), 2.01 (m,2H), 1.65 (m, 2H).

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 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; ELI LILLY AND COMPANY; GARDINIER, Kevin Matthew; GERNERT, Douglas Linn; HAHN, Patric James; HOLLINSHEAD, Sean Patrick; KHILEVICH, Albert; MAYHUGH, Daniel Ray; ORNSTEIN, Paul Leslie; PORTER, Warren Jaye; REEL, Jon Kevin; SCHKERYANTZ, Jeffrey Michael; SPINAZZE, Patrick Gianpietro; STEVENS, Freddie Craig; WITKIN, Jeffrey Michael; (199 pag.)WO2015/183673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13958-86-6, 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. 13958-86-6, name is 5-Methylpyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

3,4-diamino-5-methylpyridine (413 mg, 3.35 mmol)Mixed with 20 ml of dimethyl oxalate,Warm to reflux and stir for 3-4 hours.After the reaction solution was cooled, the resulting solid was filtered off.The solid was dispersed in 15 ml of N,N-dimethylformamide.Add 1 g of activated carbon, raise the temperature to reflux, and filter it hot after 1 hour.Add 1 ml of water to the filtrate.Allow to stand for 1 hour,The precipitated white solid is filtered,Washed with water, washed with 95% ethanol,Ethyl acetate wash to give 8-methyl-6-azaquinoxaline-2,3-dione white solid(434 mg, yield 73.1%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13958-86-6, 5-Methylpyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Jiao Tong University; Wang Yongxiang; Fu Lei; Xie Dongsheng; Lu Jun; (37 pag.)CN103435561; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6332-56-5, 3-Nitropyridin-2(1H)-one, 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, Safety of 3-Nitropyridin-2(1H)-one, blongs to pyridine-derivatives compound. Safety of 3-Nitropyridin-2(1H)-one

(1a-1) To a solution of 2-hydroxy-3-nitropyridine (Aldrich, 3.0 mmol, 420 mg) in 1,4-dioxane (20 mL), were added 4-fluorophenyl boronic acid (Combi-block, 6.0 mmol, 840 mg), copper(II) acetate (Aldrich, 4.5 mmol, 815 mg) and pyridine (2 mL). The reaction was heated at 80 C. for 20 h. After cooling to room temperature, 30 mL of cold water was added. The solid formed was collected by filtration, washed with ammonium hydroxide and water, and dried under vacuum to give 1-(4-fluorophenyl)-3-nitropyridin-2(1H)-one (610 mg, 87% yield) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6332-56-5, 3-Nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78136; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86873-60-1, 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. 86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, 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-Chloro-2-pyridinecarboxylic acid (0.176 g, 1.12 mmol) was dissolved in MeOH (5 mL) and DMTMM (0.37 g, 1.34 mmol) was added. After stirring the mixture for 5 minutes, a solution of intermediate 47 (0.25 g, 1.12 mmol) in MeOH (5 mL) was added at 0 C, and the mixture was stirred for an additional 16 h. After that, the reaction mixture was quenched with NaOH (1M in H20) at 0 C and then extracted with EtOAc. The organic layer was washed with brine, then separated, dried (MgS04) and the solvent evaporated in vacuo. The crude material was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol/DCM 0/100 to 5/95), the desired fractions were collected and the solvent evaporated in vacuo to afford compound 91 (0.215 g, 53%). Compound 91 was then purified by preparative SFC on Chiralpak Diacel AD (20 x 250 mm), mobile phase (C02, iPrOH with 0.2% iPrNH2), the desired fractions were collected, evaporated, dissolved in MeOH and evaporated again yielding compound 85 (0.061 g, 15% yield) and compound 86(0.064 g, 15.8%) yield) as pure enantiomers (both as solid compounds).

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 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; ROMBOUTS, Frederik, Jan, Rita; TRESADERN, Gary, John; VAN GOOL, Michiel, Luc, Maria; MACDONALD, Gregor, James; MARTINEZ LAMENCA, Carolina; GIJSEN, Henricus, Jacobus, Maria; WO2011/154431; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7584-05-6, 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.7584-05-6, name is 3-Methylisonicotinonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

3-Methylisonicotinonitrile (123, 590 mg, 5.0 mmol), NBS (1.2 g, 7.0 mmol) and AIBN (50 mg, 0.3 mmol) were diluted with carbon tetrachloride (20 mL); and the mixture was heated at reflux for 2 h. The reaction mixture was concentrated to one-half its original volume, filtered, and the filtrate was evaporated to dryness under reduced pressure.

Statistics shows that 7584-05-6 is playing an increasingly important role. we look forward to future research findings about 3-Methylisonicotinonitrile.

Reference:
Patent; CUSHMAN, Mark S.; KISELEV, Evgeny A.; MORRELL, Andrew E.; US2014/18360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19346-43-1, 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.19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, molecular weight is 156.1145, as common compound, the synthetic route is as follows.

To 2-ethoxyethan-1 -amine (0.659 g, 7.40 mmol) in DMF (10 mL) were added 2-fluoro-4- methyl-3-nitropyridine (1 .05g, 6.73 mmol) and K2C03 (1 .022 g, 7.40 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was diluted with water (30 mL) and extracted with EtOAc (4 x 20 mL). The organic extracts were combined and washed with brine, dried over MgS04, filtered, and concentrated. Purification by chromatography on silica gel (0 to 30% EtOAc/hexanes) afforded N-(2-ethoxyethyl)-4- methyl-3-nitropyridin-2-amine (1 .52 g) as an orange color oil. LC-MS (ES) m/z = 226 [M+H]+. NMR (400 MHz, DMSO-c/6): 5 1 .1 1 (t, J =7.0 Hz, 3H), 2.39 (s, 3H), 3.46 (q, J = 6.8 Hz, 2H), 3.50 – 3.55 (m, 2H), 3.56 – 3.63 (m, 2H), 6.64 (d, J = 4.8 Hz, 1 H), 7.54 (t, J = 5.1 Hz, 1 H), 8.16 (d, J = 4.8 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 19346-43-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); 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. 6200-60-8, name is Imidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Imidazo[1,2-a]pyridine-3-carboxylic acid

A stirring mixture of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (10 mg, 0.064 mmol) and 5-(5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (125) (21 mg, 0.064 mmol) in ethylacetate (1 mL) was added propylphosphonic anhydride solution 50 wt. % in ethyl acetate (76 uL, 0.128 mmol). The reaction was heated at 70 C. for 3 hours. The reaction was cooled to room temperature and diluted with a solution of saturated sodium bicarbonate. The organic was separated and washed with 2¡Á water/brine mixture and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography using DCM:EtOAc:MeOH (1:1:0.1). N-(5-(5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F97). 1H NMR (400 MHz, d6-DMSO) delta 10.06 (s, 1H), 9.47-9.44 (m 1H), 8.59 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.83 (dd, J=1.6, 7.6 Hz, 1H), 7.80-7.78 (m, 1H), 7.55-7.50 (m, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.20-7.16 (m, 1H), 3.76-3.68 (m, 1H), 3.38 (s, 3H), 2.88-2.85 (m, 4H), 2.36 (s, 3H) MS m/z 471.15 (M+1)+.

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, 6200-60-8, Imidazo[1,2-a]pyridine-3-carboxylic acid.

Reference:
Patent; IRM LLC; YEH, Vince; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; US2013/59846; (2013); 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. 103-74-2, name is 2-(2-Hydroxyethyl)pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Hydroxyethyl)pyridine

Aqueous HBr (2.5 L) was charged into a clean and dry round bottom flask followed by compound (9) (250 g, 2.03 mol) and heated to 120 C with azeotropical removal of water (-24 h). The residual water was removed by co-distillation with toluene (2 x 2 L), thesolid was stined in MTBE: IPA (1:1) for 1 h and filtered, washed with MTBE (200 ml) and dried in vacuum, yielding 360 g (66%) of light pink solid (compound (10)).

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, 103-74-2, 2-(2-Hydroxyethyl)pyridine.

Reference:
Patent; MAPI PHARMA LTD.; MAROM, Ehud; RUBNOV, Shai; (44 pag.)WO2016/132343; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 769-28-8, 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. 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, molecular formula is C8H8N2O, 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.

4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (20.0 g, 0.135 mol) was added to a solution of EtONa prepared from Na (3.1 g,0.135 mol) and EtOH (50 ml); the mixture was stirred for30 min, and the solvent evaporated to dryness. 4-Methylphenacyl bromide (28.8 g, 0.135 mol) and dry DMF (100 ml)was added to the resulting salt. The reaction mixture was heated on water bath at 80C for 2 h, cooled to room temperature, poured into ice water, and the formedprecipitate was filtered off. The mixture of N- and-alkylated isomers obtained in this way could be separated by two methods. Method I is based on differencein solubility of these substances (isomer 4b is less solublein CHCl3 and EtOAc than isomer 4). To separate theisomers, the obtained precipitate was placed on a Schott filter and washed with CHCl3-EtOAc, 1:1, several times.The substance remaining on the filter was recrystallized from EtOH. Method II involves the use of colum nchromatography (gradient eluting through SiO2, eluent CHCl3 followed by EtOAc).

According to the analysis of related databases, 769-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Babaev, Eugene V.; Nevskaya, Aleksandra A.; Dlynnikh, Ilya V.; Chemistry of Heterocyclic Compounds; vol. 51; 3; (2015); p. 269 – 274; Khim. Geterotsikl. Soedin.; vol. 51; 3; (2015); p. 269 – 274,6;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem