Category: pyridine-derivatives

Electric Literature of 29241-65-4, 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.29241-65-4, name is 5-Bromo-2-chloronicotinic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.45, as common compound, the synthetic route is as follows.

Add 25g Compound 1 to 75ml methanol,Cool to 0 , add 62.89g thionyl chloride dropwise,After the drop, the temperature is raised to room temperature for 2d;Sampling LCMS, the raw materials are basically reacted, most of the methanol is distilled off,The residue was poured into ice water, extracted with EA, the organic phases were combined, washed with salt, dried,Spin to dry to obtain 22.7g crude product.The crude product is directly invested in the next step.

The chemical industry reduces the impact on the environment during synthesis 29241-65-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Changsen Pharmaceutical Co., Ltd.; Wang Zhe; Zhang Jiyong; Zeng Zhihong; (105 pag.)CN111039942; (2020); A;,
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 1079054-78-6, name is 5-Amino-6-methylpicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1079054-78-6

l,l’-Thiocarbonyldiimidazole (368 mg, 1.96 mmol, 95 mass%) and then hydrochloric acid in dioxane (0.89 mL, 3.6 mmol, 4 mol/L) were added to a solution of 5-amino-6-methylpicolinonitrile (250 mg, 1.78 mmol, 95 mass%) in DCM (8.9 mL) under air. The reaction was stirred at r.t. for 24.5 hours before being concentrated in vacuo and purified by flash column chromatography on silica (gradient elution with 0% to 100% EtOAc in isohexanes) to give the title compound (176 mg, 56 % Yield). LCMS [M+H]+ 176, RT 0.93 minutes (Method 7).

With the rapid development of chemical substances, we look forward to future research findings about 1079054-78-6.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); 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. 15103-48-7, name is Pyridine-2-sulfonic acid, molecular formula is C5H5NO3S, 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. HPLC of Formula: C5H5NO3S

Pyridine-2-sulfonic acid (100 mg, 0.628 mmol) was dissolved inwater (15 ml) and added dropwise to the 7 ml of silver(I) nitrate aqueoussolution (106.7 mg; 0.628 mmol). The reaction mixture was stirredconstantly for 5 min and then allowed to stand at room temperature(pH=2.7) in the absence of light. Crystals formed by slow evaporation(after two weeks) were filtered off and used for further characterization. Yield: 57%. Elemental analysis (C5H4Ag1N1O3S1):Calcd (%) C 22.57; H 1.51; N 5.28; S 12.05 Found: C 22.50; H 1.30; N5.27; S 11.98; MS(-) m/z: 422.7 [2 M-Ag]-, 688.1 [3 M-Ag]-, 157.7[M-Ag]- (M=Ag(py-2-SO3)) (Fig. S1).

With the rapid development of chemical substances, we look forward to future research findings about 15103-48-7.

Reference:
Article; Rendo?ova, Michaela; Vargova, Zuzana; Sabolova, Danica; Imrichova, Natalia; Hudecova, Daniela; Gyepes, Robert; Lakato?, Boris; Elefantova, Katarina; Journal of Inorganic Biochemistry; vol. 186; (2018); p. 206 – 216;,
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. 7112-38-1, name is 3-(Hydrazinylmethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-(Hydrazinylmethyl)pyridine

General procedure: A mixture of 12a (12.6 g, 69.9 mmol), methylhydrazine (6.4 g,139 mmol), trifluoroacetic acid (10.7 mL, 144 mmol), and triethylamine (19.4 mL, 139 mmol) in 2-propanol (350 mL) was stirred at 80 C for 1 h, and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, and washed with saturated NaHCO3 solution and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residuewas purified by column chromatography on silica gel with hexane/ethyl acetate as an eluent to give 13c (10.0 g, 75%). The compound 13b, 13e,f, 13h-o were prepared in a manner similar to that described for 13c. Yield (19 %). 1H NMR (300 MHz, CDCl3) delta 2.32 (3H, s), 5.34 (2H, s),6.16 (1H, s), 7.07-7.17 (2H, m), 7.22-7.30 (2H, m), 7.48-7.56 (1H,m), 7.72 (1H, d, J = 8.1 Hz), 8.28-8.40 (1H, m), 8.63 (1H, d, J = 4.0 Hz).

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, 7112-38-1, 3-(Hydrazinylmethyl)pyridine.

Reference:
Article; Hasui, Tomoaki; Ohyabu, Norio; Ohra, Taiichi; Fuji, Koji; Sugimoto, Takahiro; Fujimoto, Jun; Asano, Kouhei; Oosawa, Masato; Shiotani, Sachiko; Nishigaki, Nobuhiro; Kusumoto, Keiji; Matsui, Hideki; Mizukami, Atsushi; Habuka, Noriyuki; Sogabe, Satoshi; Endo, Satoshi; Ono, Midori; Siedem, Christopher S.; Tang, Tony P.; Gauthier, Cassandra; De Meese, Lisa A.; Boyd, Steven A.; Fukumoto, Shoji; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5428 – 5445;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-17-7, 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. 58481-17-7, name is Methyl 2-(hydroxymethyl)isonicotinate. A new synthetic method of this compound is introduced below.

Methyl 2-(hydroxymethyl)isonicotinate (2.232 g, 13.35 mmol) dissolved in THF (15 mL) and phenol (1.426 mL, 16.02 mmol) and triphenylphosphine (3.71 mL, 16.02 mmol) were added. The mixture was cooled to 0 C. (E)-diisopropyl diazene-1,2-dicarboxylate (3.24 g, 16.02 mmol) was added dropwise, the ice-bath removed and the reaction stirred at room temperature for 2 h. The solvent was evaporated and the residue was purified by automated flash chromatography on a Biotage KP-SIL 340 g column. 4:1 of EtOAc in heptane over 10 CV was used as mobile phase. Methyl 2-(phenoxymethyl)isonicotinate (2.65 g, 82%) was isolated. 1H NMR (400 MHz, cdcl3) delta 3.96 (s, 3H), 5.26 (s, 2H), 6.95-7.04 (m, 3H), 7.27-7.34 (m, 2H), 7.76-7.80 (m, 1H), 8.10 (s, 1H), 8.75 (d, 1H). MS m/z 244 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-17-7, Methyl 2-(hydroxymethyl)isonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16744-81-3, 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. 16744-81-3, name is 4-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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.

A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with MeOTf (116 muL, 1.06 mmol) by micropipette. The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with 4-methoxy-2-pyridinecarboxaldehyde (Astatech C10253, 145 mg, 106 mmol) and was dissolved in PhMe (1 mL). The solution of pyridine was added via syringe onto the MeOTf at room temperature. The vial which contained the pyridine was rinsed with PhMe (0.5 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. After 20 h, hexanes (2 mL) were added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The solid or oil was then rinsed with several portions of hexanes followed by diethyl ether. Residual solvent was then removed in vacuo to provide the compound N-methyl-4-methoxy-2-pyridinecarboxaldehyde triflate (300 mg, 94percent). This oil was used for oxime formation without further purification. A flask was charged with NaOCH3 (18 mg, 0.34 mmol) and hydroxylamine hydrochloride (27 mg, 0.39 mmol) and the solids were taken up in MeOH (1 mL) and left at room temperature for 5 min. The preceding aldehyde (79 mg, 0.26 mmol) was dissolved in MeOH (2 mL) and was injected into the solution of hydroxylamine. After 18 hr at room temperature, the reaction was diluted with ethyl ether, filtered through sand, and concentrated in vacuo. The residue was purified by C-18 reverse phase chromatography (water/acetonitrile, 0-100percent) and concentrated under a stream of air, which afforded compound 101 (18 mg, 22percent) as a crystalline salt.

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 16744-81-3, 4-Methoxypicolinaldehyde.

Reference:
Patent; University of Iowa Research Foundation; Quinn, Daniel; Topczewski, Joseph John; US2014/323473; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1079179-12-6, 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.1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine, molecular formula is C5H2ClFN2O2, molecular weight is 176.53, as common compound, the synthetic route is as follows.

Preparation 59 (S)-1-(3-Fluoro-5-nitropyridin-2-yl)pyrrolidin-3-ol To a mixture of NaH (227 mg, 5.68 mmol, 60%) in DME (30 mL) was added (S)-pyrrolidin-3-ol (494 mg, 5.68 mmol) and the reaction was stirred at room temperature for 1 hour. A solution of 2-chloro-4-fluoro-5-nitropyridine (250 mg, 1.42 mmol) in DME (10 mL) was added at 10 C. and stirred at room temperature for 1 hour. The reaction was quenched with water (30 mL) and extracted with EtOAc (100 mL*2). The organic layers were combined, concentrated in vacuo and purified by silica gel column chromatography eluting with 0-50% EtOAc in petroleum ether to afford the title compound (250 mg, 77%) as yellow solid. The following preparations were prepared according to the method described by Preparation 59 using the appropriate fluoropyridine as described.

Statistics shows that 1079179-12-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-fluoro-5-nitropyridine.

Reference:
Patent; PFIZER INC.; Fensome, Andrew; Gopalsamy, Ariamala; Gerstenberger, Brian S.; Efremov, Ivan Viktorovich; Wan, Zhao-Kui; Pierce, Betsy; Telliez, Jean-Baptiste; Trujillo, John I.; Zhang, Liying; Xing, Li; (104 pag.)US2016/52930; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100367-55-3, 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. 100367-55-3, name is 5-Nitropicolinonitrile. A new synthetic method of this compound is introduced below.

4) 1864.7 g of reduced Fe powder was added to 16780 g of ethyl acetate and 1864.7 g of 2-cyano-5-nitropyridine,Oil bath heated to 81 began to drop 8299g of acetic acid, acetic acid was added dropwise to maintain a steady reflux, with the dropping of reflux temperature byGradually rise to 89 , and the need to be added within 310min was completed; after completion of the dropwise addition at 81 reaction temperature incubated for 5h.5) The reaction solution obtained in step 4) was filtered while hot at 65 C, the filtrate, the filter cake separately treated, wherein the filtrate withNaOH temperature was controlled at 5 ~ 10 , pH adjusted to 8.5, with ethyl acrylate back to the aqueous phase; to the filter cake was added the amount of propyleneEthyl acetate and NaHSO3 aqueous solution, warmed to 60 C, stirred for 15min and filtered, again with ethyl acrylate back to the aqueous phase; mergeThe organic phase obtained above was washed with saturated NaCl solution and then concentrated. Finally, 1270 g of tan solid B, 2-cyano-5-Aminopyridine, yield 85.3%, purity 97%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-55-3, 5-Nitropicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Silver Yunxin Biological Technology Co., Ltd.; Pan Jincheng; Li Shoude; Pan Shangguang; (7 pag.)CN106810494; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83766-88-5, Adding some certain compound to certain chemical reactions, such as: 83766-88-5, name is 2-(tert-Butoxy)pyridine,molecular formula is C9H13NO, 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 83766-88-5.

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.

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. 83766-88-5, 2-(tert-Butoxy)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1133879-69-2, 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. 1133879-69-2, name is 3-Fluoro-5-vinylpyridine, molecular formula is C7H6FN, 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 procedure: A mixture of tetrahydrocarbazole 5a (0.17 g,1 mmol), 5fluoro3vinylpyridine (6) (0.12 g, 1 mmol), CsF(0.1 g), and hydroquinone (0.02 g) in DMSO (1.5 mL) was heated with stirring at 130-140 C for 4 h, DMSO was evaporatedin vacuo (3 Torr), the product was extracted from residue withdichloromethane. The solvent was evaporated and the residuewas subjected to chromatography on silica gel (60 mesh), eluentmethanol-chloroform = 1 : 5. The yield was 0.22 g (75%), m.p.65-67 C. Found (%): C, 77.63; H, 6.43; N, 9.64. C19H19FN2.Calculated (%): C, 77.52; H, 6.45; N, 9.52. 1H NMR (DMSOd6), : 1.81 (m, 4 H, CH2); 2.29 (m, 2 H, CH2); 2.72 (m, 2 H,CH2); 3.05 (t, 2 H, CH2Py, J = 6.8 Hz); 4.25 (t, 2 H, CH2N,J = 6.9 Hz); 6.80 (dt, 1 H, CHPy, JHF = 9.3 Hz, JHH = 2.4 Hz);7.05-7.30 (m, 3 H, CHAr); 7.50 (d, 1 H, CHAr, J = 6.8 Hz); 8.14(s, 1 H, CHPy); 8.34 (d, 1 H, CHPy, JHH = 2.4 Hz). 19F NMR(DMSOd6), : -49.38 (d, JFH = 9.4 Hz).

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 1133879-69-2, 3-Fluoro-5-vinylpyridine.

Reference:
Article; Sokolov; Aksinenko; Nikolaeva; Grigor’Ev; Kinzirsky; Bachurin; Russian Chemical Bulletin; vol. 63; 5; (2014); p. 1137 – 1141; Izv. Akad. Nauk, Ser. Khim.; 5; (2014); p. 1137 – 1141,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem