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.33252-63-0, name is 5-(Trifluoromethyl)pyridin-2-ol, molecular formula is C6H4F3NO, molecular weight is 163.1, as common compound, the synthetic route is as follows.Application In Synthesis of 5-(Trifluoromethyl)pyridin-2-ol

lambda/-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5-(trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 mL) and the precipitate was collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated.The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol (2nd crystal : 9.65 g, total:37.75g, 85 % yield) as a yellow solid.1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1H), 8.02 (d, 1H), 13.17 (br, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-63-0, 5-(Trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); 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 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H5ClN2

General procedure: To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (2.0 g, 13.1 mmol) dissolved in DMF (30.5 mL, 0.944 g/mL, 393.2 mmol) at 0C was added portionwise sodium hydride (1.1 g, 28.8 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and l-bromobutane (2.1 mL, 1.27 g/mL, 19.7 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHC03 sat solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; gradient Heptane/EtOAc from 100/0 to 50 /50) to yield 1-1 (2.7 g, 98.7%) as a yellow liquid

With the rapid development of chemical substances, we look forward to future research findings about 60290-21-3.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (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. 73870-24-3, name is 4-(Bromomethyl)pyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-(Bromomethyl)pyridine hydrobromide

Sodium hydride {3.0 g, 125 mmol, 10 eq. (5.0 g of 60%> NaH in oil)} was added to a solution of galeterone (1, 5.0 g, 12.9 mmoL, 1 eq.) in THF (80 mL) at 0C under argon atmosphere. A white precipitate formed and after stirring for one minute, DMF (5.0 mL) was added and the reaction mixture was allowed to stir for 10 minutes at room temperature. The reaction mixture was placed at 0C and lithium carbonate (5.0 g, 67.7 mmoL, 5 eq. ) was added, followed immediately by 4-(bromomethyl)pyridine hydrobromide (14, 10 g, 39.5 mmoL, 3 eq.) and the reaction mixture was allowed to stir at 0C for 30 minutes. The reaction mixture was removed from 0C and stirring continued at ambient temperature for 18 hours under argon atmosphere. The color of the reaction mixture changed from clear to dark red during the 18-hour period. After 18 hours, the reaction mixture was placed at 0C, water (30 mL) was added to quench unreacted NaH, and the mixture was stirred for 10 minute. Volatile (THF) were removed in vacuo and water (70 mL) was added to the residue aqueous phase. The aqueous phase was extracted with ethyl acetate (EtOAc) (150 mL x 3). Ethyl acetate extract was washed with brine (80 mL x 2), dried with anhydrous Na2SO4 and concentrated in vacuo to give a dark red crude product. Purification by flash chromatography using 3% MeOH/EtOAc as eluent afforded compound galeterone 3beta-pyridine methoxylate (3) as a white solid (3.78 g, 7.88 mmoL, 61%), mp 177-179C. Rf= 0.31 (5% MeOH/EtOAc).

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, 73870-24-3, 4-(Bromomethyl)pyridine hydrobromide.

Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE; NJAR, Vincent C.O.; PURUSHOTTAMACHAR, Puranik; MURIGI, Francis; (33 pag.)WO2017/223320; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, 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.

B) 4- (Benzyloxy) -1- (2-ethyl-l-methyl-lH-benzimidazol-6- yl) pyridin-2 ( 1H) -one A mixture of 4-benzyloxy-2 ( 1H) -pyridone (1 g) , 6-bromo-2- ethyl-l-methyl-lH-benzimidazole (1.19 g) , Nu,Nu’- dimethylethylenediamine (0.530 ml), copper (I) iodide (0.946 g) , potassium carbonate (2.06 g) and DMSO (20 ml) was stirred at 150C for 2 h. The mixture was added to 28% NH3 solution, and the precipitate was collected. The solid was dissolved in THF, passed through NH silica pad and concentrated in vacuo to give the title compound (986 mg) as a pink solid. A part of the target compound was treated with activated carbon and recrystallized from THF to give 46.1 mg of the title compound as a white solid. . MS (ESI+) : [M+H]+ 360.4. XH NMR (400 MHz, DMSO-d6) : delta 1.33 (3H, t, J = 7.4 Hz), 2.90 (2H, q, J = 7.5 Hz), 3.74 (3H, s), 5.16 (2H, s), 5.98 (1H, s) , 6.10 (1H, d, J = 5.4 Hz), 7.07 (lH, d, J = 8.8 Hz), 7.34-7.51 (5H, m) , 7.53 (1H, s) , 7.55-7.62 (2H, m)

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 70298-89-4, Adding some certain compound to certain chemical reactions, such as: 70298-89-4, name is 2,2-Dimethyl-N-pyridin-4-yl-propionamide,molecular formula is C10H14N2O, 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 70298-89-4.

General procedure: To a stirred solution of 1a (0.36 g, 2.0mmol) in THF (5 mL) at ?78 C was added n-BuLi (1.6 M in hexane; 4.0 mmol) dropwise. After 15 min,temperature was raised to 0 C and stirring was continued for 2.5 h. Then, the mixture was cooled to ?78C and MeCOCO2Me (0.20 g, 2.0 mmol) was added dropwise. The resulting mixture was graduallywarmed to 0 C, treated with saturated aqueous NH4Cl (20 mL), and extracted with AcOEt (3 × 15 mL).The combined extracts were washed with brine (15 mL), dried (Na2SO4), and concentrated by evaporation.The residue was purified by column chromatography on SiO2 (AcOEt/hexane 1:3) to afford 2a (0.28 g,50percent);

According to the analysis of related databases, 70298-89-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kobayashi, Kazuhiro; Kosuna, Risa; Chikazawa, Yuuki; Heterocycles; vol. 92; 9; (2016); p. 1643 – 1653;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 105250-17-7 ,Some common heterocyclic compound, 105250-17-7, molecular formula is C6H8N2O, 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-aminopyridin-4-yl)methanol (5.00 g, 40.3 mmol) and aqueous hydrobromic acid (50 mL, c =. 48 percent , 440 mmol) was heated at 100D for 24 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. Ethyl acetate was added to the crude product and the resulting solid was filtered, washed with ethyl acetateand dried under reduced pressure to give 7.70 g (71 percent) of the title compound as a crude product that was used without further purification.LC-MS (Method 2): R = 0.68 mm; MS (ESIpos): m/z = 186; 188 [M+H]1H-NMR (400 MHz, d6-DMSO): oe [ppm] = 8.10 (brs, 2H), 7.90 (d, J = 6.9 Hz, IH), 6.98 (s,1 H), 6.84 (dd, J = 1.8 and 6.9 Hz, 1 H), 4.65 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,105250-17-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 166526-03-0 ,Some common heterocyclic compound, 166526-03-0, molecular formula is C6H2Cl2N2, 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 2,4-dichloro-5-cyanopyridine (1 Og, 57.8 mmol), fe/f-butyl carbamate (8.2 g, 70.5 mmol), Pd(OAc)2 (0.26 g, 1 .1 mmol), Xantphos (1 .34 g, 2.3mmol) and K2C03 (12 g, 87 mmol) in THF (150 mL) was degassed 3x with nitrogen. The mixture was then heated at 70 C for 4-5 h and monitored by chromatography until complete conversion. Following completion of the reaction, additional THF (100 mL) was added and heated the mixture at 70 C for additional 1 h and then cooled to room temperature. The suspension was then filtered through a pad of celite to remove the solid. The filtrate was then concentrated and azotropically distilled with ethyl acetete before filtering to give the title compound. 1 H NMR (DMSO-d6, 400 MHz): delta 10.82 (s, 1 H), 8.79 (s, 1 H), 8.09 (s, 1 H), 1 .49 (s, 9H).

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. 166526-03-0, 4,6-Dichloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOEPFEL, Thomas; LEBLANC, Catherine; MAH, Robert; MALLET, Franck; MARTZ, Julie; LIAO, Lv; XIONG, Jing; HAN, Bo; WANG, Can; ZHAO, Xianglin; (56 pag.)WO2016/151500; (2016); 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. 18368-64-4, name is 2-Chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-methylpyridine

In a 1000 mL flask 450 g of chlorobenzene, 100 g of 2-chloro-5-methylpyridine and 3 g of cobalt acetate were added with stirring. The temperature of the heating system was raised to 80° C and the flow rate of oxygen was controlled at 0.4 L / Min and under these conditions the reaction was carried out for 4 hours. After completion of the reaction, the system was cooled to room temperature, filtered and dried to give 119 g of a mixture of 6-chloronicotinic acid and cobalt acetate. The above resulting mixed crude product was placed in a 1000 mL flask, then added 600 g of recrystallized solvent methanol, stirring heated to reflux until all the crude 6 – chloro nicotinic acid was dissolved, after 5 min of incubation, the system slowly cooled to 5°C, white crystal was precipitated, the stirring was continued for 1 hour while maintaining the internal temperature , then carried out flirtation , the filter cake was washed once with a small amount of cooled methanol and obtained product was dried at 80°C for 4 hours to obtain 98.5 g of 6-chloronicotinic acid, Purity 99. 52percent (HPLC), yield 79.7percent( Do not count the remaining product in the mother liquor, followed by a slightly written as “excluding the mother liquor”).

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, 18368-64-4, 2-Chloro-5-methylpyridine.

Reference:
Patent; CHANGSHU LEAGUE CHEMICAL CO LTD; CHEN, HUA; (6 pag.)CN103570612; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-16-7, 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 571189-16-7 as follows.

A suspension of 2 and 10% palladium on carbon in ethanol was hydrogenated for 2 h. The reaction mixture was filtered through celite and concentrated in vacuo to give 3 as brown oil. 1H NMR (400 MHz, DMSO-d6): delta 7.77-7.76 (d, J = 2.1 Hz, 1H, ArH), 7.27-7.14 (dd, J = 3.0 Hz, 1H, ArH), 6.51 (d, J = 9.0 Hz, 1H, ArH), 3.61-3.59 (m, 4H, piperazine-CH2), 3.39-3.36 (m, 4H, piperazine-CH2), 1.48 (s, 9H. t-butyl-CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Article; Sharath Kumar, Kothanahally S.; Hanumappa, Ananda; Hegde, Mahesh; Narasimhamurthy, Kereyagalahally H.; Raghavan, Sathees C.; Rangappa, Kanchugarakoppal S.; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 341 – 349;,
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. 142-08-5, name is Pyridin-2(1H)-one, the common compound, a new synthetic route is introduced below. Formula: C5H5NO

(128-2) Under nitrogen atmosphere, to a solution of 2-hydroxypyridine (2.66 g) and NEt3 (4.05 mL) in THF (80 mL) was added dropwise SOCl2 (1.05 mL) under ice-cooling, and the mixture was stirred for one hour. The mixture was filtered, and the solvent was evaporated under reduced pressure to give di-2-pyridyl sulfite (3.02 g, 91 %).

The synthetic route of 142-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1479384; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem