Category: pyridine-derivatives

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); 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. 623585-74-0, name is Methyl 2,5-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 2,5-dichloroisonicotinate

To a cold solution of methyl 2,5-dichloroisonicotinate (500 mg, 2.42 mmol) in THF (15 mL) was added N-Methyl-2-pyrrolidone (1.4 mL), iron(III)acetyl acetone (43 mg, 0.12 mmol) and methyl magnesium bromide (36 mg, 0.305 mmol) at 0C. The reaction mixture was stirred at 0C for 1 h and then at rt for 18 h. The reaction mixture was quenched with brine and was extracted with ethyl acetate. The organic layer was separated, dried, filtered and concentrated to afford 130 mg of the title product.1H NMR (300 MHz, DMSO d6): delta 8.46 (s, 1H), 7.74 (s,lH), 3.87 (s, 3H), 2.44 (s, 3H).

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, 623585-74-0, Methyl 2,5-dichloroisonicotinate.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/72825; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1197294-80-6, 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 1197294-80-6, name is tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate (1.00 g, 2.66 mmol), 5-chloro-2-hydroxyphenylboronic acid (458 mg, 2.66 mmol) and sodium carbonate (1.13 g, 10.64 mmol) were combined and dissolved in a mixture of dioxane/water (14 mL/4 mL). The reaction mixture was degassed for 20 min with nitrogen and then tetrakistriphenylphosphinepalladium (0) (153 mg, 0.133 mmol) was added. The reaction mixture was heated at 70 C. for 18 hours and then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was separated, washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (10% to 60% ethyl acetate in heptane over 20 CV) to give the title compound (700 mg, 66%) as a white solid.1H NMR (400 MHz, CD3OD): delta 1.40 (s, 9H), 3.50 (s, 8H), 6.80-6.90 (m, 2H), 6.95 (s, 1H), 7.15 (d, 1H), 7.30 (s, 1H), 8.05 (d, 1H).LCMS Rt=2.48 minutes MS m/z 388 [M-H]-.

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 1197294-80-6, tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; ICAGEN INC.; PFIZER LIMITED; US2012/10182; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

Production Example 14 (1) [0776] A mixture of 5.14 g of 3-amino-2-chloro-5-trifluoromethylpyridine, 3.92 g of zinc cyanide, 1.19 g of tris(dibenzylideneacetone)dipalladium(O), 1. 45 g of 1,1′-bis (diphenylphosphino) ferrocene and 20 ml of DMF was stirred at 150C for 40 minutes. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate and washed with water, and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and then the resulting residue was applied to a silica gel column chromatography to obtain 2.23 g of 3-amino-2-cyano-5-trifluoromethylpyridine. 3-Amino-2-cyano-5-trifluoromethylpyridine 1H-NMR(CDCl3)delta: 8.29(1H, d), 7.33(1H, d), 4.70(2H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; TAKAHASHI, Masaki; ITO, Mai; NOKURA, Yoshihiko; TANABE, Takamasa; SHIMIZU, Chie; EP2865671; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 52605-96-6, 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 52605-96-6, name is 2-Chloro-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the product of step 1 (12.8 g, 89.16 minol) in TFIF (100 mL) at .-70 was added LDA (67 rnL) dropwise. After stirring for 40 mm, a solution of 12 (29.5 g, 116rnmol) in THF (50 rnL) was added dropwise. The mixture was stirred at -70 C for 5 h, sat, aq. NHCl added and the mixture extracted with EtOAc (100 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica (10% EtOAc in petroleum ether) to give the title compound as a solid. LRMS miz (M+H) 269.1 found, 269.1 required.

According to the analysis of related databases, 52605-96-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

(Synthesis of aromatic compound P2)Aromatic compound P2 was synthesized according to the following reaction formula. [Chemical Formula 119]Aromatic compound P2[0139] First, compound 2(l,4-bis-(2-bromo-4-methylpyridm-6-yl)-3,4-diaminobenzene) to be used as the starting material was synthesized via 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole.[0140] Specifically, 4.930 g of 2,6-dibromo-4-methylpyridine (0.0196 mol) and 0.762 g of 4,7-bis-pinacolato-diborane-2,l ,3-benzothiadiazole (0.00196 mol) were dissolved in 120 ml of toluene to obtain a toluene solution. To the toluene solution there were added 10 ml of an aqueous solution dissolving 10 g of K2C03, and 0.032 g of trioctylmethylammonium chloride (trade name: Aliquat336 by Aldrich Co., hereunder referred to as “Aliquat336”). After deaerating the solution with argon, 0.1132 g of tetrakis-(triphenylphosphin)-Pd(0)(0.098 mmol) was added and the mixture was heated at 80C for 1 week. This was followed by column purification (dichloromethane/hexane/ethyl acetate) to obtain 0.507 g of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole at a yield of 54% .Results of NMR analysis and MS analysis of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2, 1 ,3-benzothiadiazole-NMR (250 MHz, CD2C12): delta = 8.684 ppm (s, 2H); 8.625 ppm (s, 2H); 7.385 ppm (s, 2H); 2.484 ppm (s, 6H)MS(FD, 8 kV) Found: m/z 476.2 (M ), Calculated: m/z: 476.19 (M+)

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. 73112-16-0, 2,6-Dibromo-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Max Planck Gesellschaft zur Foerderung der Wissenschaften e. V.; KOSHINO, Nobuyoshi; HIGASHIMURA, Hideyuki; MUELLEN, Klaus; MALOTKI, Christian von; SU, Qi; BAUMGARTEN, Martin; NOROUZI-ARASI, Hassan; ARNOLD, Lena; LIU, Ruili; WO2011/52805; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 61494-55-1, 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 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows.

The title compound is synthesized following the procedures of Ting, P. C. et al., J. Med. Chem., 33, 2697 (1990), as follows. A stirred mixture of (2-chloropyridin-3-yl)acetic (400 mg, 2.3 mmol), aniline (456 muL, 5.0 mmol), tosic acid (10 mg) and pentanol (5 mL) is heated at reflux for 24 hr. After cooling to room temperature, water (80 mL) is added and the mixture is extracted with ethyl acetate-25% dichloromethane. The organic layer is separated, dried, filtered and concentrated. The residue is purified by chromatography eluting with dichloromethane-0 to 5% methanol. The product containing fractions are combined and concentrated to afford 1-phenyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (356 mg, 76%) as a light brown solid. MS 211 (M+H).

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 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54631; (2005); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of sodium hydride [(1 .52 g, 63.17 mmol (95%)] in DMSO (20.0 mL) at 0 00 diethylmalonate (10.11 g, 63.17 mmol) was added and kept for reflux at 100 00 forlh. The reaction mixture was cooled to room temperature and intermediate 32b(10.0 g, 42.11 mmol) was added drop wise in DMSO (20 mL) to the resulting solutionand refluxed at 10000 for 3 h. The reaction mixture was quenched with ice water and extracted by using Ethyl acetate washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo to yield the title compound (10.0 g, 75.00%) as a brown oily product. LOMS: (M-H) = 315.0

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, 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.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

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 83766-88-5, 2-(tert-Butoxy)pyridine.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
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. 769-54-0, name is 3-Fluoro-4-nitropyridine 1-oxide, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Fluoro-4-nitropyridine 1-oxide

To a mixture suspension of 3-fluoro-4-nitropyridine 1-oxide (9.75 g, 61.7 mmol) and methanol (145 mL) was added 28% sodium methoxide methanol solution (11.9 g, 61.7 mmol) with cooling with ice. This mixture was heated to room temperature and stirred for 1 hour at the temperature. The methanol was distilled off under reduced pressure. Water (50 mL) was added to the residue, followed by extracting with chloroform. The organic layer was washed with brine, and anhydrous sodium sulfate was added to dry the layer. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure to obtain 3-methoxy-4-nitropyridine 1-oxide (9.54 g; yield, 91%).

The synthetic route of 769-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; KIRIYAMA, Kazuhisa; MATSUMOTO, Masahiro; YOSHIDA, Kotaro; BOLDBAATAR, DamdinSuren; JUKUROGI, Tatsuya; UMEMOTO, Nao; KANI, Tatsuya; MATSUDA, Yoko; TANAKA, Kumiko; KANUMA, Michiko; SHIMADA, Tatsuya; WO2014/98259; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem