Category: pyridine-derivatives

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.88482-17-1, name is 5-Amino-2-methylisonicotinic acid, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.Quality Control of 5-Amino-2-methylisonicotinic acid

Preparation 2 6-Methyl-pyrido[3,4-d]pyrimid-4-one 5-Amino-2-methyl-4pyridinecarboxylic acid was prepared according to Palt, K.; Celadnik, M.; Dvorackova, D.; Kubala, E., Cesk. Farm., 32(8), 275-278 (1983). This carboxylic acid was converted to the title product by heating in formamide at 165 C. according to the procedure of Robins, R.; Hitchings, G.; J. Am. Chem. Soc. 77, 2256 (1965).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88482-17-1, 5-Amino-2-methylisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US6395733; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65-22-5, 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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride. A new synthetic method of this compound is introduced below.

In a round bottom flask containing 7 mL methanol and 3 mL of DMF was added the diamine N2S2-4C¡¤2HCl (0.1 mmol; 0.038 g), pyridoxal hydrochloride (0.2 mmol; 0.041 g) and 60 muL of triethylamine. The resulting suspension was heated at 60 C with magnetic stirring and then was added nickel perchlorate (0.1 mmol; 0.036 g). The resulting mixture was stirred at 60 C for 45 min. After this period, the flask contents the solution was cooled to room temperature and filtered. Red crystals were collected after 4 days by slow evaporation of the solvent. Yield (crystals): 84%. Melting point: up 250 C. IR (KBr pellets cm-1): nu(O-Halcohol) 3362 s, nu(Caliphatic-H) 2929 w, nu(C = N) 1602 s, nu(C = O DMF) 1654 s, nu(C-S) 761 m,. Anal. Calc.: C, 54.67; H, 5.24; N, 9.11. Found: C, 54.60; H, 5.49; N, 8.98.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65-22-5, 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Fontana, Liniquer Andre; Stueker, Monica; Oliveira, Gelson Manzoni; Iglesias, Bernardo Almeida; Back, Davi Fernando; Inorganic Chemistry Communications; vol. 62; (2015); p. 55 – 59;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 136888-21-6, 2-Chloro-5-fluoro-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, Quality Control of 2-Chloro-5-fluoro-3-nitropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Chloro-5-fluoro-3-nitropyridine

2-Chloro-3-nitro-5-fluoropyridine (353 mg, 2.0 mmol),Copper powder (317 mg, 5.0 mmol) was added to 6 ml of anhydrous DMF solution under a nitrogen atmosphere.Heated to 150 C for 10 hours under nitrogen protection,After adding ammonia water and extracting with ethyl acetate, after removing the low boiling point solvent,Separation by column chromatography (silica gel, eluent: ethyl acetate / petroleum ether = 1/10)A pure 3-amino-3′-hydroxy-(2,2′)-bipyridine derivative was obtained.The product was a pale yellow solid with a yield of 54%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136888-21-6, 2-Chloro-5-fluoro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Nanchang University; Cai Hu; Liu Qing; Xie Yongfa; Yue Shusheng; (11 pag.)CN107935924; (2018); A;,
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. 1480-65-5, name is 5-Chloro-2-fluoropyridine, molecular formula is C5H3ClFN, 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. Application In Synthesis of 5-Chloro-2-fluoropyridine

A solution of n-butyllithium (2.7N in heptanes; 165 mL, 445 mmol) in THF (300 mL) was cooled to -78¡ãC and treated with 2,2,6,6-tetramethylpiperidine (77 mL, 456 mmol). The reaction mixture was allowed to stir for 30 minutes. A solution of 5-chloro-2- fluoropyridine (50.0 g, 380 mmol) in THF (200 mL) was added drop wise over 30 minutes. After stirring for an additional 30 minutes, the reaction mixture was quenched by bubbling CO2 through the reaction mixture for 10 minutes. The reaction mixture was allowed to warm to RT, and CO2 was bubbled through for an additional 30 minutes. The reaction mixture was then concentrated under reduced pressure and dissolved in DMF (400 mL). 4-Bromo-3-fluorophenol (72.6 g, 380 mmol) was added, followed by potassium carbonate (68.3 g, 494 mmol). The reaction mixture was heated to 120 ¡ãC overnight. The reaction mixture was diluted with EtOAc and washed with 4N HC1. The organic layer was separated, washed with water and dried over MgS04. The solvent was removed under reduced pressure. The crude residue was dissolved in Eaton’s Reagent (700 mL, 54.0 g, 380 mmol) and the reaction mixture was heated to 120 ¡ãC overnight. The reaction mixture was poured onto a mixture of ice and MeOH. The resulting solid was filtered off and washed with water. The solid was suspended in a mixture of MeOH (100 mL) and cyclopropyl methyl ether (200 mL) and filtered off. The grey solid was washed with hexanes and dried yielding 7-bromo-3-chloro-8-fluoro-5H-chromeno[2,3- b]pyridin-5-one (53.76 g, 164 mmol, 43.0 percent yield) as a ~4:1 mixture of isomers.

With the rapid development of chemical substances, we look forward to future research findings about 1480-65-5.

Reference:
Patent; AMGEN INC.; WHITE, Ryan; CHENG, Yuan; MINATTI, Ana Elena; YANG, Bryant; ZHENG, Xiao Mei; LOPEZ, Patricia; HUMAN, Jason B.; EPSTEIN, Oleg; JUDD, Ted; SHAM, Kelvin; XUE, Qiufen; WO2013/44092; (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. 1737-93-5, name is 3,5-Dichloro-2,4,6-trifluoropyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5Cl2F3N

3,5-Dichloro-2,4,6-trifluoropyridine (2.01 g, 9.95 mmol) was ssolved in tetrahydrofuran (40 mL) and cooled to -78 C. ethylmagnesium chloride (6.2 mL, 12.40 mmol) was added slowly to the cooled solution and stirred for 30 minutes. Gradually allowed to warm to 0 C and monitored by LCMS until disappearance of starting material. Worked up with EtOAc (3x) and aq. saturated NaHCO3. The combined organics were washed with brine, dried over magnesium sulfate, filtered and gently concentrated to afford a volatile yellow oil.

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, 1737-93-5, 3,5-Dichloro-2,4,6-trifluoropyridine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 120034-05-1, Methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate, 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, Computed Properties of C7H6BrNO3, blongs to pyridine-derivatives compound. Computed Properties of C7H6BrNO3

The compound prepared in the above Step 1 (300 mg, 1.29 mmol) was dissolved in dichloromethane, and 4-fluorophenylboronic acid (543 mg, 3.88 mmol), anhydrous copper (II) acetate (469 mg, 2.58 mmol), and pyridine (0.42 mL, 5.16 mmol) were sequentially added to this solution. The mixture was stirred at room temperature for 24 hours. The mixture was filtered through a celite pad and then extracted with dichloromethane. The separated organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain the title compound (0.14 g, yield: 36%, yellow solid). 1H NMR (500MHz, DMSO-d6) d 8.30 (s, 1H), 8.16 (s, 1H), 7.54-7.50 (m, 2H), 7.39-7.34 (m, 2H), 3.76 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,120034-05-1, Methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; WELLMARKER BIO CO., LTD.; LEE, Hyunho; PARK, Chun-Ho; HUR, Sun Chul; MOON, Jai-Hee; SHIN, Jae-Sik; HONG, Seung-Woo; PARK, Yoon-Sun; KIM, Joseph; LEE, Sohee; KIM, Hyojin; PARK, Hyebin; (83 pag.)WO2019/182274; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 154078-83-8, 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 154078-83-8, name is Ethyl 2-(3-nitropyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 2-(3-nitropyrid-2-yl)acetate (1.05 g, 5 mmol, 1.0 eqin DMF (10 mL) was added DMF-DMA (0.9 g, 7.5 mmol, 1.5 eq). The mixture was stirred at rt overnight. The mixture was poured into water (50 mL), extracted with EA (50 mL x 2). The organic layer was washed with water (50 mL x 2) and brine (50 mL x 2), dried over sodium sulfate, concentrated to afford ethyl 3-(dimethylamino)-2-(3-nitropyrid-2-yl)propenoate (650 mg, 50%) which was used in next step directly. LCMS: (M+H)+: 265.9.

According to the analysis of related databases, 154078-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1346575-64-1, 3-(Aminomethyl)-6-methyl-4-propylpyridin-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, 1346575-64-1, blongs to pyridine-derivatives compound. Product Details of 1346575-64-1

To a cooled (0 C.) mixture of 6-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid (400 mg, 1.37 mmol) in DMF (10 mL) was added EDC.HCl (310 mg, 1.65 mmol) and HOBt.H2O (250 mg, 1.65 mmol). The reaction was stirred for 15 min, then DIPEA (1.2 mL, 6.89 mmol) and 3-aminomethyl-6-methyl-4-propyl-1H-pyridin-2-one (240 mg, 1.37 mmol) were added. The reaction was allowed to warm to RT and stirred for 16 h, at which time it was diluted with water (20 mL) and extracted with DCM (2¡Á15 mL). The combined DCM layer was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography eluting with 3% MeOH in chloroform and then further purified by preparative HPLC to furnish 6-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid (6-methyl-2-oxo-4-propyl-1,2-dihydro-pyridin-3-ylmethyl)-amide (120 mg, 19%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 0.92-0.88 (t, 3H), 1.43-1.41 (d, J=6.8 Hz, 6H), 1.56 (m, 2H), 2.12 (s, 3H), 2.22 (s, 6H), 2.55-2.53 (m, 2H), 2.06 (m, 2H), 4.11-4.09 (t, 2H), 4.36-4.34 (d, J=4.8 Hz, 2H), 4.76-4.73 (m, 1H), 5.90 (s, 1H), 6.74-6.73 (d, J=2.8 Hz, 1H), 7.04 (s, 1H), 7.20 (s, 1H), 7.43-7.42 (d, J=3.2 Hz, 1H), 8.10-8.07 (bs, 1H), 11.55 (bs, 1H). LCMS (ES+): m/z=453.23 [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,1346575-64-1, its application will become more common.

Reference:
Patent; Bassil, Anna K.; Beinke, Soren; Prinjha, Rabinder Kumar; US2014/256739; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55676-22-7, 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.55676-22-7, name is 3-Acetyl-6-chloropyridine, molecular formula is C7H6ClNO, molecular weight is 155.5816, as common compound, the synthetic route is as follows.

To a mixture of 1-(6-chloro-pyridin-3-yl)-ethanone (0.50 g, 3.2 mmol), ferrocenecarboxaldehyde (0.69 g, 3.2 mmol), and lithium hydroxide (0.08 g, 3.2 mmol), in a 10 mL solution of water and ethanol (1/1), at room temperature, was applied an ultrasonic agitation for 10 seconds (amplitude = 0.3; ti = 29C, tf = 29C; E = 366 J). The tries of crystallization of the mixture did not provide any pure compound, thus, it was purified by flash chromatography (silica column, CH2Cl2:MeOH = 1:0 to 9:1) to give pure 1i (0.37 g, 1.1 mmol, 32.9% yield) as a dark red/purple solid. 1i: mp 209-211 C (EtOH); Rf (CH2Cl2:MeOH = 99:1) = 0.5; 1H NMR (DMSO[d6], 400 MHz) delta ppm 4.21 (s, 5H, ferrocenyl-H), 4.60 (s, 2H, ferrocenyl-H), 4.89 (s, 2H, ferrocenyl-H), 7.44 (d, J = 15.2 Hz, 1H, CHCHCO), 7.71 (d, J = 8.3 Hz, 1H, ArH), 7.74 (d, J = 15.2 Hz, 1H, CHCHCO), 8.43 (dd, J = 8.3, 2.6 Hz, 1H, ArH), 9.08 (d, J = 2.6 Hz, 1H, ArH); 13C NMR (CDCl3, 100 MHz) delta ppm 69.3 (2 CH ferrocenyl), 70.0 (5 CH ferrocenyl), 72.0 (2 CH ferrocenyl), 78.5 (C ferrocenyl), 117.9 (CH), 124.5 (CH), 132.8 (C), 138.5 (CH), 149.1 (CH), 149.7 (CH), 154.8 (C), 186.8 (C); IR nu (cm-1): 1652, 1584, 1363, 1312, 1095, 1015, 977, 748; Anal. Calcd for C18H14ClFeNO: C, 61.49; H, 4.01; N, 3.98. Found: C, 61.90; H, 4.12; N, 4.18%.

Statistics shows that 55676-22-7 is playing an increasingly important role. we look forward to future research findings about 3-Acetyl-6-chloropyridine.

Reference:
Article; Dubois, Joelle; Farce, Amaury; Ghinet, Alina; Homerin, Germain; Nica, Adrian Sorin; Bioorganic and medicinal chemistry letters; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98400-69-2, 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 98400-69-2, name is 4-(Boc-Amino)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: These were made using MSH or DNPH as detailed below, unless otherwise stated. A fresh solution of MSH23 in CH2Cl2 (1 equiv) was added to the substituted pyridine (1 equiv) in CH2Cl2 (10 mL) at 0 ¡ãC. After 2 h, the solvent was removed in vacuo. Alternatively, a solution of DNPH12 (1 equiv) and the substituted pyridine (1 equiv) in MeCN (40 mL) was heated at 40 ¡ãC for 18 h. The solvent was removed in vacuo. The method continues by taking the residue from either method in dry DMF (8 mL), and then ethyl propiolate (1 equiv) and K2CO3 (2 equiv) were added, and the suspension stirred at room temperature for 18 h. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed three times with water then with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient, unless otherwise stated) gave the pyrazolo[1,5-a]pyridine.

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 98400-69-2, 4-(Boc-Amino)pyridine.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Fre?de?rick, Raphae?l; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem