Day: April 6, 2022

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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. A new synthetic method of this compound is introduced below., SDS of cas: 107867-51-6

To a solution of 3-(4-bromophenyl)oxetane-3-carboxylic acid (550.0 mg, 2.139 mmol) in DCM (15.0 mL) was added HATU (976 mg, 2.57 mmol). The reaction was stirred for 10 min. Then to the reaction mixture were added 5-(trifluoromethyl)pyridine-2,3-diamine (379 mg, 2.14 mmol), DIEA (1.12 mL, 6.42 mmol) and reaction was stirred at RT for 12 h. The reaction was diluted with EtOAc and washed with 3 portions of 1 N HC1, 2 portions of water, 1 portion of brine, 1 portion of NaHCCb (sat.). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (EtOAc in DCM : 0-1005% gradient) to afford the title compound. MS (EI) m/z 416 [M+H]+.

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, 107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); 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. 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

1. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (grams) (65 mmol (millimole)) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL (milliliter) of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge, 2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63-64 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 57.2; %H, 5.73; %N, 22.1 1 H NMR (nuclear magnetic resonance spectrum (200 megahertz)) CDCl3:7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13C NMR CDCl3:152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

The synthetic route of 19346-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5614469; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 872355-55-0, 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 872355-55-0 as follows.

6-Methyl-lH-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.65 g) and 4-fluorobenzyl- 2S,5R-dimethyl piperazine (0.82 g) were dissolved in dry DMF (10 mL) and TBTU (1.18 g) was added followed by triethylamine(l .54 mL). The mixture was stirred for 5 h, whereupon it was poured into water and the solid thus separated was filtered and dried. The crude was purified by silica gel chromatography using ethyl acetate as a solvent (Yield: 0.87 g, Rf. 0.767min, Condition B, M+H+: 380).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,872355-55-0, its application will become more common.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1796-84-5, 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 1796-84-5, name is 4-Ethoxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 1-N,N-Dimethylcarbamoyl-4-methoxycarbonyl-3-[5-(N-3-nitropyridin-4-yl)aminomethylthien-2-oyl]indole. To a solution of 1-N,N-dimethylcarbamoyl4-methoxycarbonyl-3-(5-aminomethylthien-2-oyl)indole (0.896 g, 2.33 mmol) in CH3 CN (5 mL) was added 4-ethoxy-3-nitropyridine (0.428 g, 2.55 mmol) and the reaction mixture was heated at reflux for 17 hours, then the solvent was removed in vacuo and the residue heated at 100 C. for 2 hours. The reaction mixture was then put under high vacuum to give 1-N,N-dimethylcarbamoyl-4-methoxycarbonyl-3-[5-(N-3-nitropyridin-4-yl)aminomethylthien-2-oyl]indole as a brown foam which was used without further purification.

According to the analysis of related databases, 1796-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US5486525; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3, Adding some certain compound to certain chemical reactions, such as: 156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine,molecular formula is C7H5ClN2, 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 156072-84-3.

Step 2: Synthesis of 5-chloro-3-methylpicolinic acid To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5.0N (110 ml, 550 mmol). The resulting mixture was refluxed at 90 C. for 18 h. After cooling to RT, the reaction mixture was concentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2*). The aqueous layer was again acidified with 5N HCl to pH 4 and extracted with EtOAc (2*). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C. for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).

According to the analysis of related databases, 156072-84-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0 ,Some common heterocyclic compound, 628691-93-0, molecular formula is C6H3ClFNO2, 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.

Carbonyldiimidazole (1.80 g, 1 1.1 mmol) was added to a solution of 2-chloro-3-fluoro- isonicotinic acid (1.3 g, 7.41 mmol) in THF (21.2 mL). The reaction mixture was stirred at RT overnight and was then added to a cold (0C) solution of NaBH4 (1.40 g, 37 mmol) in water (52.9 mL). The mixture was stirred for 10 min at 0C, and 1 M HCI was then added carefully to quench the reaction (caution: H2 evolving). Volatiles were removed via rotary evaporation and the residue was dissolved in saturated aqueous NaHC03. The mixture was extracted repeatedly with CH2CI2, the combined organics were dried (phase separator) and concentrated in vaccuo. Purification by flash column chromatography on silica gel (eluent gradient: c- hexane/EtOAc 4: 1 to 2: 1) afforded the title compound as a white solid. TLC, Rf (c- hexane/EtOAc 1 :1) = 0.37; MS (LC/MS): 162.0 [M+H]+; tR (HPLC conditions b): 1.60 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

240 mg (1.19 mmol) of 2-chloro-5-(trifluoromethyl)pyridin-3-amine and 357 mg (1.31 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid were dissolved together with 0.39 ml (4.78 mmol) of pyridine in 20 ml of dioxane, 367 mg (2.39 mmol) of phosphoryl chloride were added, and the mixture was stirred at reflux for 90 min. The mixture was concentrated, the residue was taken up in ethyl acetate and washed with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography purification with a cyclohexane/ethyl acetate gradient (80:20 to 40:60) as eluent. (log P (neutral): 5.71; MH+: 412; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 1.37 (t, 3H), 3.12 (q, 2H), 7.74-7.84 (m, 2H), 8.07-8.14 (m, 2H), 8.49 (s, 1H), 8.70 (s, 1H), 9.02 (s, 1H), 11.12 (s, 1H).

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; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083057-12-8, 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 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows.

The 3-butyl 3-(3-methylpyridin-2-yl)benzoate (1.0 eq.) was dissolved in EtOAc (6 EtOAc). Water (0.3 vol) and hydrogen peroxide urea (3 eq.) were added in that order. Phthalic anhydride (3 equivalents) was then added portionwise to the mixture in solid form at a rate to maintain the temperature in the reactor below 45 C. After the addition of phthalic anhydride was completed, the mixture was heated to 45 C. After stirring for another 4 hours, the heater was turned off. A 10% w/w aqueous Na2SO3 solution (1.5 eq.) was added via an addition funnel. After the addition of Na2SO3 was completed, the mixture was stirred for additional 30 min and the layers were separated. The organic layer was stirred and a 10% wt/wt aqueous Na2CO3 solution (2 eq.) was added. After stirring for 30 minutes, the layers were separated. The organic phase was washed with a 13% w/v NaCl aqueous solution. The organic phase was then filtered and concentrated to give crude 2-(3-(t-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) which was used directly in the next step .

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, MARINUS JACOBUS; ALARGOVA, ROSSITZA GUEORGUIEVA; KAUSHIK, RITU ROHIT; KADIYALA, IRINA NIKOLAEVNA; YOUNG, CHRISTOPHER; (118 pag.)TWI636051; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256785-86-0, 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.1256785-86-0, name is 1-(4-Aminopyridin-2-yl)ethanone, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.

Example 20 (2R,5S)-N-(2-Acetyl-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide While stirring with ice-cooling, 12.5 ml of trifluoroacetic acid was added to 12.5 ml of chloroform solution containing 1.41 g of 2-acetyl-4-pyridinylcarbamic acid t-butyl ester.. The mixture was immediately warmed up to room temperature and stirred for 2 hours and 40 minutes.. The solvent was evaporated under reduced pressure to obtain a crude amine.. This compound was dissolved in 25 ml of pyridine, and the solution was mixed with 0.83 ml of phenyl chloroformate while stirring with ice-cooling and then immediately warmed up to room temperature.. After 8 hours and 30 minutes, this was mixed with 10 ml of pyridine solution containing 1.4 g of (2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile and heated under reflux for 1 hour.. The reaction mixture cooled to room temperature was mixed with water and extracted with chloroform.. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by a silica gel column chromatography to obtain 1.03 g of the title compound from methanol-chloroform (1:99, v/v) elude. NMR: 1.10 (3H, d, J=7), 1.20 (3H, d, J=7), 2.61 (3H, s), 3.34-3.52 (2H, m), 3.75 (1H, d, J=14), 3.92 (1H, d, J=14), 4.28-4.45 (1H, m), 4.46-4.62 (I H, m), 7.20-7.35 (2H, m), 7.78-7.91 (2H, m), 8.12 (1H, d, J=2), 8.48 (1H, d, J=6), 9.24(1H, s)

The chemical industry reduces the impact on the environment during synthesis 1256785-86-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co. Ltd.; US6673799; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90395-45-2 ,Some common heterocyclic compound, 90395-45-2, molecular formula is C13H11NO, 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.

1-(4-Pyridin-3-ylphenyl)-ethanone (33 g, 166.8 mmole),3,5-Dibromo-benzaldehyde (42.06 g, 159.34 mmole), and 840 ml of ethanol were added to the reaction flask for stirring.Finally, sodium tert-butoxide (22.94 g, 239 mmole) was added and stirred at room temperature.After the reaction has been completed, 200 ml of deionized water is added and stirred for filtration. The solid is filtered and washed with deionized water and methanol. The solid is then filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes, and repeated twice. Dry the solid to give 55 g of pale yellow solid 3-(3,5-dibromophenyl)-1-(4-pyridin-3-ylphenyl)-acetone(3-(3,5-Dibromo-phenyl)-1-(4-pyridin-3-yl-phenyl)-propanone),The yield was 77.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90395-45-2, its application will become more common.

Reference:
Patent; E-ray Optoelectronics Technology Co Ltd; Huang, Heh Lung; Guo, Huang Ming; Chao, Teng Chih; Lin, Chi Jen; Chang, Min Jong; (53 pag.)TW2019/30287; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem