Category: pyridine-derivatives

Application of 869557-43-7, 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.869557-43-7, name is 2-Amino-3-bromo-5-fluoropyridine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

(8a) 3-Bromo-2,5-difluoropyridine Sodium nitrite (1.97 g, 28.6 mmol) was added in small portions to a solution of 3-bromo-5-fluoropyridin-2-amine (WO20062578 A1, 3.64 g, 19.1 mmol) in hydrofluoric acid pyridine (10 mL) at -10C. After stirring at room temperature for two hours, water (100 mL) and sodium bicarbonate were added to the reaction mixture at 0C, followed by extraction with ethyl acetate (100 mL). Then, the organic layer was washed with water (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride) to obtain the title compound (1.56 g, 42%) as a brown liquid. 1H-NMR (400 MHz, CDCl3): delta ppm: 7.78 (1H, dt, J = 2.7, 6.7 Hz), 8.02 (1H, dd, J = 1.6, 2.4 Hz).

The chemical industry reduces the impact on the environment during synthesis 869557-43-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2404918; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1180132-17-5, 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. 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine, molecular formula is C12H20N4, 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: To a solution of 5a (0.10 g, 0.33 mmol) and 9a (0.07 g, 0.33 mmol) in 1,4-dioxane (2 mL), were added Cs2CO3 (0.21 g, 0.65 mmol), Pd2(dba)3 (0.03 g, 0.03 mmol) and XantPhos (0.03 g, 0.06 mmol). The mixture was heated to 120 C for 60 min with microwave, then cooled to room temperature, diluted with water (10 mL), and extracted with DCM (40 mL × 3). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4, concentrated under vacuum, and purified by silica gel column chromatography (DCM / MeOH = 20:1) to give compound 10a (0.02 g, 12.40%) as a yellow solid.

According to the analysis of related databases, 1180132-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yan; Liu, Wen-Jian; Yin, Lei; Li, Heng; Chen, Zhen-Hua; Zhu, Dian-Xi; Song, Xiu-Qing; Cheng, Zhen-Zhen; Song, Peng; Wang, Zhan; Li, Zhi-Gang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 974 – 978;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 84703-18-4, Adding some certain compound to certain chemical reactions, such as: 84703-18-4, name is 5-Bromo-2-chloro-6-methylnicotinonitrile,molecular formula is C7H4BrClN2, 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 84703-18-4.

General procedure: A mixture of 10a-10k (1 mmol), methyl thioglycolate (159 mg,1.5 mmol) and Et3N (152 mg, 1.5 mmol) in 10 mL of methanol was stirred at 80 C for 6-8 h. Methanol was removed under vacuum.The residuewas purified by column chromatography to provide thetitle compound.

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. 84703-18-4, 5-Bromo-2-chloro-6-methylnicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Yan; Li, Min; Li, Bowen; Zhang, Shun; Su, Aoze; Xing, Yongning; Ge, Zemei; Li, Runtao; Yang, Baoxue; European Journal of Medicinal Chemistry; vol. 172; (2019); p. 131 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 897732-75-1, 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. 897732-75-1, name is 2-Methyl-6-(methylsulfonyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

EXAMPLE 55; 3-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)-N-(2-methyl-6-(methylsulfonyl) pyridin-3-yl)-[l,2,4]triazolo[4,3-b]pyridazin-8-amineStep 1: 3,6-Dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4- amine [0394] A 100-mL round-bottom flask was charged with a solution of 2-methyl- 6-(methylsulfonyl)pyridin-3-amine (500 mg, 2.69 mmol) in tetrahydrofuran (50 mL), sodium hydride (269 mg, 11.2 mmol), and 3,4,6-trichloropyridazine (1 g, 5.49 mmol). The resulting solution was stirred for 16 hrs at room temperature. The reaction was then quenched with brine (50 mL), extracted with ethyl acetate (4×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a residue. This residue was purified by a silica gel column chromatography eluted with dichloromethane/ethyl acetate (2/1) affording 3,6-dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4-amine as pale yellow solid (0.75 g, 84%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,897732-75-1, 2-Methyl-6-(methylsulfonyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
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. 67346-74-1, name is 3-Ethynylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Ethynylpyridin-2-amine

Reference Example 59 3-(3-(4-(4-Fluoro-pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (3 mL) solution of (4-(4-fluoro-pyridin-2-yloxymethyl)-phenyl)-acetohydroximoyl chloride (200 mg, 0.679 mmol) described in Manufacturing Example 59-1-5 and 3-ethynyl-pyridin-2-ylamine (50 mg, 0.423 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (237 muL, 1.7 mmol) at room temperature, which was stirred for 4 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1-1:1) to obtain the title compound (57 mg, 22percent).1H-NMR Spectrum (CDCl3) delta (ppm): 4.09 (2H, s), 5.09 (2H, s), 5.84 (2H, brs), 6.30 (1H, s), 6.74-6.77 (1H, m), 6.80-6.82 (1H, m), 6.90-6.91 (1H, m), 7.33-7.42 (3H, m), 7.76-7.78 (1H, m), 8.09-8.11 (1H, m), 8.19-8.21 (2H, m).

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, 67346-74-1, 3-Ethynylpyridin-2-amine.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
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. 73998-95-5, name is (4,6-Dichloropyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 73998-95-5

To a stirred solution of 41A (2.5 g, 14 mmol) in CH2Cl2 (20 mL) was added slowly SOCl2 (1.2 mL, 14 mmol) at room temperature. The reaction was stirred for 15 minutes, cooled to 0 C. and washed with saturated aqueous NaHCO3. The CH2Cl2 layer was dried (MgSO4), concentrated in vacuo and purified by flash chromatography (SiO2, CH2Cl2) to give 41B (1.3 g, 47%).

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, 73998-95-5, (4,6-Dichloropyridin-3-yl)methanol.

Reference:
Patent; Gavai, Ashvinikumar V.; Norris, Derek J.; Han, Wen-Ching; Vite, Gregory D.; Fink, Brian E.; Tokarski, John S.; US2005/192310; (2005); 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. 86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, 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. Safety of 5-Chloro-2-picolinic acid

General procedure: To a solution of the picolinic acid S7 (25.0 mmol) in DCM (100 mL) at room temperature was added SOCl2 (20 mL) and some drops of dry DMF. The reaction was allowed to stir at 50 C for 3 hours. The solvent was then removed under reduced pressure to afford the corresponding crude acid chloride (S8). Then DCM (40 mL) was added and the solution was cooled to 0C followed by dropwise addition of NEt3 (75.0 mmol, 3.0 eq) and N,O-dimethylhydroxylamine (50.0mmol, 2.0 eq). The reaction mixture was stirred at rt overnight, extracted by DCM, the organic layerwas dried over Na2SO4 and the solvent was evaporated, then purified by flash chromatography to gain the corresponding amides (S9).

With the rapid development of chemical substances, we look forward to future research findings about 86873-60-1.

Reference:
Article; Jin, Liang; Yao, Qi-Jun; Xie, Pei-Pei; Li, Ya; Zhan, Bei-Bei; Han, Ye-Qiang; Hong, Xin; Shi, Bing-Feng; Chem; vol. 6; 2; (2020); p. 497 – 511;,
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. 1122-54-9, name is 4-Acetylpyridine, molecular formula is C7H7NO, 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 4-Acetylpyridine

General procedure: Substrate scope and enantioselectivity determination The relative activities of 26 substrates were measured using thepreviously described assay protocol with adjusted ratio of enzymeand substrate concentration. The a-chloroacetophenone activitywas assumed 100%.Enantioselectivity was determined by examining the reductionof aromatic ketones using an NADH-regeneration system consist-ing of the puried KcDH and glucose dehydrogenase (GDH) fromBacillus subtilis CGMCC 1.1398. The 1-mL reaction mixture con-tained 0.5 mM NAD+, 10 mM ketone, 1 U KcDH, 50 mg glucoseand 2 U GDH in 50 mM potassium phosphate buffer (pH 7.0). After16 h, the reaction sample was equally separated into two parts,with one terminated by adding an equal volume of methanol, fol-lowed by HPLC analysis to determine the conversion ratio, and theother extracted with ethyl acetate, followed by ee analysis. Meth-ods used for analysing chiral products using HPLC or GC aredescribed in Supplementary Table S1.

With the rapid development of chemical substances, we look forward to future research findings about 1122-54-9.

Reference:
Article; Wu, Kai; Chen, Lifeng; Fan, Haiyang; Zhao, Zhiqiang; Wang, Hualei; Wei, Dongzhi; Tetrahedron Letters; vol. 57; 8; (2016); p. 899 – 904;,
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. 98027-84-0, name is 2,6-Dichloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,6-Dichloro-4-iodopyridine

Example 1A 6-chloro-N-cyclohexyl-4-iodopyridin-2-amine A mixture of 2,6-dichloro-4-iodopyridine (5 g, 18.3 mmol) and cyclohexylamine (18.1 g, 183 mmol) was heated in a Biotage Initiator microwave at 150 C. for 30 min. Ethyl acetate (150 mL) was added and the mixture washed with water (100 mL) and brine (50 mL). The organics were concentrated and the residual oil purified by flash chromatography on silica gel eluding with 10% ethyl acetate in hexanes to provide the title compound. Yield: 4.7 g (76%). MS (DCI/NH3) m/z 337 (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, 98027-84-0, 2,6-Dichloro-4-iodopyridine.

Reference:
Patent; ABBOTT LABORATORIES; US2011/15172; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86873-60-1, 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 86873-60-1, name is 5-Chloro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-Chloropicolinic acid (75.6 mg, 480 muetaiotaomicron) was suspended in dichloromethane (6 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (85.2 mg, 58.8 mu, 672 mupiiotaomicron) as well as dimethylformamide (0.137 M in toluene, 87.6 mu^, 12 mupiiotaomicron) were added. The mixture was stirred for 17 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) to afford 5-chloropicolinoyl chloride as yellow oil (88.8 mg, quant.). After that, tert-butyl ((4aR,5R,9R)-5-(6-amino-3-fluoropyridin-2-yl)-3,3-difluoro-5,8,8-trimethyl-9-oxido- 2,3,4,4a,5,8-hexahydro-[l,4]thiazino[2, l-f][l,2]thiazin-7-yl)carbamate (Int-51AAp, 80 mg, 168 muiotaetaomicron) was dissolved in dichloromethane (5 mL), the solution cooled to 0-5C (ice bath) and N,N-diisopropylethylamine (82.6 mg, 111.6 muL, 640 muiotaetaomicron) was added, followed by a solution of 5-chloropicolinoyl chloride (vide supra, 88.8 mg, 480 muiotaetaomicron) in dichloromethane (6 mL). The reaction mixture was stirred for 15 min at 0-5C, followed by 3 h at room temperature. Then, an aqueous solution of sodium carbonate (10%, 15 mL) was added, the mixture was stirred for 10 min at room temperature. After phase separation, the aqueous layer was extracted the dichloromethane (2 x 10 mL), the combined organics were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 12 g, eluting with ethyl acetate / n-heptane, gradient 10:90 to 40:60) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (110 mg), that was used in the next step without further purification. HPLC (method LCMS_gradient) tR = 3.6 min. MS (ES+) m/z 615.1 [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 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem