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.124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.COA of Formula: C8H6F3NO2

IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of methyl 5-trifluoromethyl-pyridine-2-carboxylate (2 g, 9.75 mmol) in MeOH (30 mL) at 0C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93% yield): 1H NMR (400 MHz, CDC13) delta ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124236-37-9, Methyl 5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHRISTENSEN, IV, Siegfried Benjamin; WU, Chengde; ZHANG, Zhiliu; YU, Haiyu; YUAN, Jiangxing; LIN, Xiaojuan; XU, Shanli; LV, Maoyun; YAO, Chen; LI, Lei; HUANG, Xing; GAO, Min; WO2013/166621; (2013); 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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of 5-bromo-3-chloro-2-methylpyridine (1.03 g, 5 mmol) and (i-PrO)3B (2.24 mL, 10 mmol) in THF (10 mL) was added n-BuLi (3.75 mL, 1.6 M in hexane, 6 mmol) drop-wise at – 78 oC. After the mixture was stirred at -78 oC for 1 hr, it was quenched with water. The solvent was removed under reduced pressure and the aqueous layer was washed with Ether (2 x 10 mL). The aqueous layer was then adjusted to pH~8 with 1N aqueous HCl solution and extracted with EA (3 x 50 mL). The combined organic layers were dried over Na2SO4, and concentrated to give 5-chloro-6-methylpyridin-3-ylboronic acid (650 mg, 76% yield) as a white solid. Retention time (LC-MS): Retention 0.458 min. MH+ 172

The synthetic route of 914358-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertand, L.; WU, Xinyuan; (351 pag.)WO2016/44792; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77199-09-8, 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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: Ester (FAE, 4a-m, 2a or 2b) (500 mg scale, 1 equiv.) was dissolvedin 6 ml THF at 0 C in a 25 ml round-bottom flask. ThenNaOH(aq) (5 equiv.) was added dropwise and stirred for 15 h atroom temperature. After starting materials were consumed (byTLC), water (20 ml) was added. The reaction mixture was washedwith ethyl acetate (2 x 20 ml). The aqueous solution was acidified(pH 2-3) with 1 M HCl(aq) causing precipitation of a solid, whichwas filtered and dried under vacuum. Recrystallization in ethanolafford clean compound.

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 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
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. 54-92-2, name is N’-Isopropylisonicotinohydrazide. A new synthetic method of this compound is introduced below., Safety of N’-Isopropylisonicotinohydrazide

To solution containing (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid (200.0 mg, 0.70 mmol), N?-isopropylisonicotino hydrazide (188.2 mg, 1.05 mmol) and HATU (399.2 mg, 1.05 mmol) dissolved in DMF (5.0 ml), N,N-diisopropylethylamine (DIPEA)(0.18 ml, 1.05 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc=3:1) for refinement and dried so that ivory (E)-tert-butyl 3-(3-(2-isonicotinoyl-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (108 mg, 34.4%). [0353] 1H-NMR (MeOD, 500 MHz): delta 8.87 (2H, d, J=4.6 Hz, aromatic), 8.18 (1H, d, J=8.3 Hz, aromatic), 7.95 (3H, m, aromatic), 7.84 (1H, d, J=15.7 Hz, indole-CH?CH-), 7.58 (1H, m, aromatic), 7.34 (1H, t, J=7.6 Hz, aromatic), 7.13 (1H, m, aromatic), 6.96 (1H, d, J=15.2 Hz, indole-CH?CH-), 5.03 (1H, m, -N-CH-(CH3)2), 1.71 (9H, s, Boc), 1.33 (6H, m, -N-CH-(CH3)2)

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, 54-92-2, N’-Isopropylisonicotinohydrazide.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; LEE, Hyun Sun; KIM, Mun-Ock; CHOI, Yongseok; Lee, Kyeong; PARK, Jeong-Jun; SEO, Jee-Hee; JUNG, Hwayoung; CHO, Sungchan; US2014/57909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 722550-01-8, 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 722550-01-8 as follows.

General procedure: 2-(5-Bromo-2-isopropoxy-4~methoxyphenyl)-7-(pyrrolidin”l-yl)imidazo| l,2-o]~ pyridine hydrobromide 73 was prepared in the same manner as 2-(5-bromo-2,4-dimethoxy- phenyl)”7-(pyrro3idin~l~yl)imidazo[l,2-a]pyridine 9a and was obtained as an off-white solid (26% yield). 1H NMR. (400 MHz, DMSO-c 6): delta 13.04 (s, IH), 8.61 (d, J= 7.6 Hz, IH), 8.11 (s, IH), 8.02 (s, IH), 6.95 (s, H), 6.93 (s, IH), 6.27 (s, IH), 5.06-4.97 (m, IH), 3,94 (s, 3H), 3,48-3.40 (m, 4H), 2.06-1.99 (rn, 4H), 1.44 (s, 3H), 1.42 (s, 31 1 }: HPLC (Method 3) >99% (AUC), fR = 18.93 min; ESI MS m/z 4?()| M + H]+ . A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [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,722550-01-8, its application will become more common.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
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 88912-24-7, name is 5,6-Dichloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a 100 mE round bottom flask equipped with a magnetic stirrer, reflux condenser and a nitrogen inlet were added 5,6-dichioropicolinic acid (5.00 g, 23.1 mmol), TEA (8.2 g, 81.0 mmol), ACN (39.5 g) and water (15.1 g). The solution was sparged for 30 mm with nitrogen (1 mE/mm) Afier sparging, triphenylphosphine (TPP; 0.18 g, 0.686 mmol) and palladium(II) acetate (0.078 g, 0.347 mmol) were added to the solution. Furan-2-boronic acid (3.3 g, 28.9 mmol) was added in one portion, and heating was initiated. The reaction mixture was heated to 55 C., and was sampled and analyzed by liquid chromatography. No boronic acid was remaining after two hours, and heating was stopped. The reaction mixture was allowed to cool overnight and then was heated to 45 C. Once at temperature, 50% sulfuric acid (7.1 g) was added. No precipitation was observed, so the mixture was cooled. After 30 mm at <5 C., no solids were observed and water (25.7 g) was added. A precipitate formed which was allowed to cool for 1 h and isolated by filtration. The flask was rinsed with cold mother liquor to isolate all of the product. The wetcake was then rinsed with cold ACN- water solution (8.75 g and 11.25 g, respectively). The palladium content was analyzed in the wetcake, wash and mother liquors, with 81% of the palladium in the mother liquor and wash, and 19% in the wet cake. 99% of the total palladium added was recovered. With the rapid development of chemical substances, we look forward to future research findings about 88912-24-7. Reference:
Patent; Dow AgroSciences LLC; Biswas, Sanjib; Chakrabarti, Reetam; Huffman, Lauren M.; Leng, Ronald B.; Schuitman, Abraham D.; Spiers, Karin; Stottlemyer, Alan L.; Epp, Jeffrey B.; (18 pag.)US2016/340311; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57963-08-3, 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 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (0.257 g, 1.99 mmol) was added to a suspension of intermediate Z48 (0.20 g, 0.66 mmol), 5,6-dimethylpyridin-2-amine (0.097 g, 0.80 mmol) and HATU (0.38 g, 1.00 mmol) in DCM (15 mL) at 0 C. The reaction was allowed to warm to rt and was stirred for 18 h before being quenched with water, extracted with DCM (2 x 40 mL), washed with brine and dried over anhydrous Na2S04. Solvents were removed in vacuo and the crude product was purified by flash column chromatography (10% ethyl acetate in hexane) to afford intermediate Y21 (0.091 g, 0.22 mmol, 34%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta: 10.86 (1H, s), 7.95-7.93 (1H, d, J= 8.4 Hz), 7.89-7.88 (1H, d, J= 2.0 Hz), 7.81-7.79 (1H, dd, J= 8.4 Hz, 2.0 Hz), 7.56-7.54 (1H, d, J= 8.4 Hz), 7.47-7.45 (1H, d, J= 8.0 Hz), 2.35 (3H, s), 2.22 (3H, s), 1.36 (9H, s).

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 57963-08-3, 5,6-Dimethylpyridin-2-amine.

Reference:
Patent; H. LUNDBECK A/S; MALTAS, Philip James; WATSON, Stephen; LANGGARD, Morten; DAVID, Laurent; WO2014/114779; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-26-0, Adding some certain compound to certain chemical reactions, such as: 3430-26-0, name is 2,5-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 3430-26-0.

Step A: 5-Bromo-2-iodo-4-methyl-pyridine To a solution of 2,5-dibromo-4-methylpyridine (2 g) in acetonitrile (40 ml) at room temperature under argon were added sodium iodide (4.8 g) then acetyl chloride (0.94 g). After 3 hours stirring at room temperature the white solid formed was filtered off and the filtrate was neutralized with aqueous saturated solution of sodium hydrogenocarbonate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/cyclohexane) to afford the title product as a brown solid (2.04 g). 1H-NMR (CDCl3, 400 MHz): 8.40 (s, 1H), 7.60 (s, 1H), 2.30 (s, 3H),

According to the analysis of related databases, 3430-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-88-9, 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 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 15-1. 4-Iodo-N,N,3-trimethylpyridine-2-amine (Compound 15b) A DMF (7.9 mL) solution of 2-chloro-4-iodo-3-methylpyridine (Compound 15a, 500 mg, 1.97 mmol), N-ethyl-N-propan-2-ylpropane-2-amine (0.515 mL, 2.96 mmol), and a THF solution (2.96 mL, 5.92 mmol) of 2M dimethylamine was stirred at 130 C. for 17 h., then the solution was cooled to room temperature and formic acid (0.4 mL) was added. The solution was purified by reversed-phase chromatography (acetonitrile/water, 0.1% formic acid) to obtain the titled Compound 15b (258 mg, yield 50%) as a light brown solution.

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 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; YOSHINO, Hitoshi; TSUCHIYA, Satoshi; MATSUO, Atsushi; SATO, Tsutomu; NISHIMOTO, Masahiro; OGURI, Kyoko; OGAWA, Hiroko; NISHIMURA, Yoshikazu; FURUTA, Yoshiyuki; KASHIWAGI, Hirotaka; HORI, Nobuyuki; KAMON, Takuma; SHIRAISHI, Takuya; YOSHIDA, Shoshin; KAWAI, Takahiro; TANIDA, Satoshi; AOKI, Masahide; (169 pag.)US2019/225604; (2019); 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. 955372-86-8, name is 3-Bromo-5-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-Bromo-5-fluoroisonicotinic acid

TMSCHN2 (180 mL, 360 mmol, 2 equiv) was added into a solution of 3-bromo-5- fluoroisonicotinic acid (40 g, 182 mmol, 1 equiv), THF (240 mL), and MeOH (80 mL) dropwise with stirring at 0 C under nitrogen. The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1/9) to afford the title compound (35 g, 83%) as 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, 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PARAZA PHARMA, INC.; BEAUMIER, Francis; DERY, Martin; LAROUCHE-GAUTHIER, Robin; CHEN, Huifen; SHORE, Daniel; VILLEMURE, Elisia; VOLGRAF, Matthew; HU, Baihua; LU, Aijun; CRIDLAND, Andrew; WARD, Stuart; (212 pag.)WO2018/96159; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem