Day: April 7, 2022

Adding a certain compound to certain chemical reactions, such as: 113293-70-2, 2,6-Dichloroisonicotinaldehyde, 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, 113293-70-2, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Dichloroisonicotinaldehyde

To a solution of commercially available 2,6-dichloropyridine-4-carbaldehyde (0.3 g, 1.7 mmol) in CH2CI2 (34 ml.) under N2 at -78 0C is added DAST (0.67 ml_, 5.1 mmol). The reaction is allowed to warm to room temperature, stirred 1 h, and poured into cold water. The separated aqueous layer is extracted with fresh CH2CI2 The combined organic layers are dried (Na2SO4), concentrated, and purified by flash chromatography (10% EtOAc/heptanes) to yield an orange oil: 1H NMR (400 MHz, CDCI3) delta ppm 6.60 (t, J=55.1 Hz, 1 H), 7.40 (s, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13958-93-5, 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 13958-93-5 as follows.

Preparation of 3,5-Dichloro-N-[4-(2-hydroxy-ethyl)-benzyl]-isonicotinamide: Using the EDCI coupling general procedure F: Reaction of 2-(4-Aminomethyl-phenyl)-ethanol (306 mg, 2.03 mmol), 3,5-dichloroisonicotinic acid (385 mg, 2.03 mmol), 1-hydroxybenzotriazole (301 mg, 2.22 mmol), 4-methyl morpholine (0.50 mL, 4.45 mmol), and EDCI (426 mg, 2.22 mmol) in anhydrous DMF (5 mL) overnight at room temperature and overnight at 40 C. followed by column chromatography on silica gel (2:2:96 MeOH-NH4OH-CH2Cl2) gave the title compound (291 mg, 44%) as a white foam.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-93-5, its application will become more common.

Reference:
Patent; Bridger, Gary; Skerlj, Renato; Kaller, Al; Harwig, Curtis; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher Dennis; Di Fluri, Maria Rosaria; US2002/147192; (2002); 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. 54864-83-4, name is 6-Chloro-N,N-dimethylnicotinamide, the common compound, a new synthetic route is introduced below. Computed Properties of C8H9ClN2O

1 -(4-/Lery-Butylphenyl)-6-chloro-2-ethoxycarbonylmethyl-5-hydroxyindole-3- carboxylic acid ethyl ester (120 mg, 0.26 mmol, see step (b) above), 6-chloro-Lambda^7V- dimethylriicotinamide (72 mg, 0.39 mmol), K2CO3 (181 mg, 1.31 mmol) and DMF (3 mL) was heated at 115 0C for 96 h and filtered through Celite. The solids were washed with EtOAc and the combined filtrates concentrated and purified by chromatography to give the sub-title compound. Yield 48 mg (78%).

The synthetic route of 54864-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77366; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145934-89-0, 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 145934-89-0, name is 2-Chloro-5-hydrazinylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step B: 1 -(6-fluoropyridin-3-yl)-3-pyridin-3-yl-5-ftrifiuoromethyl)-4,5-dihydro-l H-pgammarazol-5-olA solution of 2-chloro-5-hydrazinopyridine (136 mg, 0.95 mmol) and acetic acid (0.29 mL, 5,00 mmol) in ethanol (2 mL) is added to a stirred solution of (lZ)-45454-trifluoro-l-pyridin-3-ylbut-l- ene-l,3,3-triol (160 mg, 0,68 mmol) in ethanol (2 mL) in a pressure tube. The reaction mixture is heated at 90 0C (oil bath temp) overnight, cooled and concentrated. The residue was purified by silica gel chromatography (2% to 10% MeOH in CH2Cl2). LRMS: m/z found: 343.5 (M+l).

According to the analysis of related databases, 145934-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/151800; (2009); 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. 142337-95-9, name is 3-Bromo-5-ethylpyridine. A new synthetic method of this compound is introduced below., Formula: C7H8BrN

Commercially available 3-acetyl-5- bromopyridine (6.53 g, 32.8 mmol), solid NaOH (13.1 g, 326 mmol), and hydrazine hydrate (13 mL) was heated in di ethylene glycol (25 mL) at 140 0C for 4 hours. The reaction mixture was partitioned between ether and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give an oil. This was dissolved in tetrahydrofuran (40 mL) and cooled to 0 0C. Isopropylmagnesiumchloride (20 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hours at room temperature. N,N-dimethylformamide (7 mL) in tetrahydrofuran (15 mL) was added and stirring was continued for. an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3- ethyl-5-formylpyridine (0.78 g, 18%) as a solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.91 (s, IH), 8.71 (s, IH), 8.00 (s, IH), 2.75 (q, 2H), 1.31 (t, 3H). MS m/z calculated for (M + H)+ 152, found 152.

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, 142337-95-9, 3-Bromo-5-ethylpyridine.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1086838-13-2, 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 1086838-13-2, name is 5-Chloro-3-nitropicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of delta-chloro-S-nitropyridine^-carboxaldehyde (1 g), described in Example 146, in 1 ,2-dichloroethane (20 mL) was added 4A molecular sieves powder and 2-(tert-butyldimethylsilanyloxy)propylamine (1.22 g) described in Example 105 part a. After stirring overnight at room temperature, sodium cyanoborohydride (0.4 g) and acetic acid (0.33 mL) were added at O0C. After stirring for one hour at O0C, the reaction mixture was heated to 65C overnight. The reaction mixture was filtered through a plug of Celite and concentrated under reduced pressure to yield a residue that was purified by chromatography (SiO2, heptane/EA) to afford 2-[2-(tert- butyldimethylsilanyloxy)propyl]-6-chloro-2/-/-pyrazolo[4,3-iotab]pyridine (0.6 g, 37%). MS(ES): M/Z [M+H]=326. 1 H NMR: (400 MHz, CHLOROFORM-d): -0.37 (s, 3H), -0.09 (s, 3H), 0.79 (s, 9H), 1.24 (d, J=6.1 Hz, 3H), 4.21 – 4.31 (m, 1 H), 4.33 – 4.38 (m, 1 H), 4.40 – 4.47 (m, 1 H), 8.00 (dd, J=2.1 , 0.9 Hz, 1H), 8.22 (d, J=O.7 Hz, 1H) and 8.48 (d, J=2.1 Hz, 1 H).

According to the analysis of related databases, 1086838-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERIAL LIMITED; AVENTIS AGRICULTURE; WO2008/144275; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

A sealed tube was charged with 16-1 (1.0 g, 2.70 mmol), Et3N (4.89 mL, 35.1 mmol) and Ethynyltrimethylsilane (4.85 mL, 35.1 mmol) and the resulting solution was degassed with Argon for about 10 minutes followed by the addition of CuI (514 mg, 2.70 mmol) and PdCl2(PPh3)2 (1.89 g, 2.70 mmol). The reaction tube was sealed and heated at 90oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was partitioned between heptane and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The crude mass was dissolved in MeOH (10 mL) and to it was added K2CO3 (713 mg, 5.16 mmol) and the solution was stirred at ambient temperature for 2 hours to produce 16-2. The reaction mass was filtered through a short bed of celite and the filtrate was concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-10% Ethyl acetate in Hexane) to afford 16-2 (462 mg, 1.46 mmol, 54%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.63 (d, J = 8.24 Hz, 1H), 7.43-7.28 (m, 10H), 7.34 (d, J = 8.16 Hz, 1H), 5.44 (s, 2H), 5.29 (s, 2H), 3.24 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33630-99-8, 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 33630-99-8 as follows.

To a mixture of 3-aminopyridin-2(1H)-one (3.25 g, 29.5 mmol) and sodium carbonate (6.26 g, 59.0 mmol) in tetrahydrofuran (100 mL) at rt was added benzylcarbonochloridate (5.27 mL, 36.9 mmol) over 5 mm. The mixture was stirred at rt for 24diluted with ethyl acetate (150 mL), and filtered through Celite. The filtrate was concentrated under vacuum to a volume of approximate 200 mL, washed with water (40 mL), and dried over anhydrous Mg504. The solution was concentrated under vacuum to a volume of approximate 50 mL. The precipitating material (the first crop of product) wascollected as a white solid by suction. The filtrate was concentrated under vacuum to almost dryness. The residue was stirred with diethyl ether (50 mL). The insoluble material (the second crop of product) was collected as a white solid by suction. The two crops of product was combined and dried at 50 C under vacuum to give the desired product, benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate (5.77 g, 23.62 mmol, 80 %yield), as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33630-99-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1026201-45-5, 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.1026201-45-5, name is 8-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.

SOCl2 (15 ml, 206 mmol) was added slowly to intermediate 39 (1.6 g, 6.6 mmol) while cooling on ice. The resulting solution was heated to reflux temperature for 4 h, and was then cooled to r.t. and concentrated in vacuo. The residue was triturated with DIPE and finally the product was dried. Yield: 1.7 g of intermediate 40 (99 %).

Statistics shows that 1026201-45-5 is playing an increasingly important role. we look forward to future research findings about 8-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, 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. Recommanded Product: 153374-33-5

The reaction was conducted according to the General Procedure by heating KOt-Bu (4.5 mg, 0.04 mmol, 20 mol%), N-methyl- 4-azaindole 3a (26.4 mg, 0.2 mmol, 1 equiv), Et3SiH (98 muL, 0.6 mmol, 3 equiv) and 0.2 mL of THF at 45 C for 96 h. C2:C3 = 6:1. A mixture of C2- and C3-silylation products (16.2 mg, 33% yield) was obtained after purification by silica gel flash chromatography (50% EtOAc in hexanes). Analytically pure C2-silylation 4a was obtained as a colorless oil after subsequent purification by Preparative TLC (50% EtOAc in hexanes). Rf = 0.1 (33% EtOAc in hexanes); 1H NMR (500 MHz, CDCl3) delta 8.44 (dd, J = 4.6, 1.4 Hz, 1H), 7.60 (dt, J = 8.3, 1.2 Hz, 1H), 7.09 (dd, J = 8.3, 4.6 Hz, 1H), 6.90 (d, J = 0.9 Hz, 1H), 3.83 (s, 3H), 1.03- 0.97 (m, 9H), 0.96- 0.89 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 147.0, 143.0, 142.7, 133.0, 116.4, 116.1, 113.8, 33.1, 7.6, 4.0. IR (Neat Film, NaCl) 2953, 2909, 2874, 1596, 1557, 1455, 1434, 1413, 1355, 1317, 1288, 1237, 1134, 1064, 1004, 800 cm-1; HRMS (ESI+) calc?d for C14H23N2Si [M+H]+: 247.1625, found 247.1621.

With the rapid development of chemical substances, we look forward to future research findings about 153374-33-5.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; GRUBBS, Robert, H.; FEDOROV, Alexey; TOUTOV, Anton; LIU, Wenbo; BETZ, Kerry; (129 pag.)WO2016/22624; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem