Pyridine-derivatives

Synthetic Route of 709652-82-4, 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below.

To a stirred solution of compound 2 (4.6 g) in HC1 (48.4 mL ) was added sodium nitrite ( 5.3 mL ) dropwise at-5 C. The reaction mixture was stirred at room temperature for 2h. The resulting solids were collected by filtration and dried in vacuum to give compound 3 (4.4 g, 88%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VITAS PHARMA RESEARCH PRIVATE LIMITED; RANGARAJAN, Radha; KUMAR, Rajinder; PRABHAKAR, B V; CHANDRASEKHAR, P; MALLIKARJUNA, P; BANERJEE, Ankita; WO2013/42035; (2013); 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.75358-90-6, name is Ethyl 2-cyanonicotinate, molecular formula is C9H8N2O2, molecular weight is 176.17, as common compound, the synthetic route is as follows.Recommanded Product: 75358-90-6

To a solution of ethyl 2-cyano-3-pyridinecarboxylate (2.5 g) and conc. HCl (5 mL) in 150 mL ethanol was added 10% Pd/C (wet, 250 mg) and the reaction mixture was hydrogenated using a hydrogen balloon and stirred for 12 h. The reaction was filtered through celite and ethanol was evaporated to give ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCl as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75358-90-6, Ethyl 2-cyanonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Global Blood Therapeutics, Inc.; The Regents of the University of Califorina; Cytokinetics, Inc.; Metcalf, Brian; Chuang, Chihyuan; Warrington, Jeffrey; Paulvannan, Kumar; Jacobson, Matthew P.; Hua, Lan; Morgan, Bradley; US2015/344483; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 97004-04-1, 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 97004-04-1 as follows.

2-(4-Trifluoromethylphenyl hydrazono) propionic acid (12.31 g, 50.0 mmol) was dissolved in dichloromethane (250 ml) and N,N-dimethylformamide (25 ml), and 5-aminomethyl-2-chloropyridine (7.13 g, 50.0 mmol) and 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloric acid salt (9.59 g, 50.0 mmol) were added thereto. 30 hours later, the mixture was washed with 1N hydrochloric acid, a saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate and then filtrated. The residue obtained by concentrating the resulting filtrate was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 63) (14.47 g, 39.02 mmol, 78%). Compound No. 63: mp 184C; 1H NMR (400 MHz, CDCl3) delta 2.16 (3H, s), 4.57 (2H, d), 7.15 (2H, d), 7.31 (2H, d), 7.35 (1H, brt), 7.54 (2H, d), 7.64 (1H, s), 7.66 (1 H, dd), 8.38 (1 H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97004-04-1, its application will become more common.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; EP1470752; (2004); 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.117873-72-0, name is 2,6-Dibromo-4-methoxypyridine, molecular formula is C6H5Br2NO, molecular weight is 266.92, as common compound, the synthetic route is as follows.COA of Formula: C6H5Br2NO

2,6-Dibromo-4-methoxy pyridine (6) was obtained in 80% yield when 2,4,6-tribromopyridine (5) was allowed to react with sodium methoxide (1.2 eq) in refluxing methanol. The compound (6) was treated using n-butyl lithium (1.2 eq.), was allowed to react with pivalonitrile (1.2 eq.) for 150 minutes at -78C and was refluxed for two hours in two normal sulfuric acid to yield ketone isomer (7) in 86% yield. An optically active alcohol (8) was obtained in 93% yield and in 90% ee optical purity from compound (7) through hydrogen transfer type asymmetric reduction of formic acid (4.3 eq.) and triethylamine (2.5 eq.) using the asymmetric ruthenium catalyst (RuCl[(S,S]-Tsdpen)(p-cumene), 0.01 eq.) as the catalyst. The compound (8) was converted to a camphor ester using the acid chloride, an optical resolution process was conducted using re-crystallization (75% yield, diastereomer ratio = >99/<1) and saponified again to obtain an almost optically pure alcohol (7, quant.). The compound (7) was subjected to homo coupling using a palladium catalyst [PdCl2(PhCN)2-TDAE] to yield a pyridine isomer (9) (Chemical formula 5) in 36% yield (diastereomer ratio =>99.5/<0.5). At the same time, in my other blogs, there are other synthetic methods of this type of compound,117873-72-0, 2,6-Dibromo-4-methoxypyridine, and friends who are interested can also refer to it. Reference:
Patent; Japan Science and Technology Agency; EP1724251; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6188-43-8, 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.6188-43-8, name is Imidazo[1,2-a]pyridine-3-carbaldehyde, molecular formula is C8H6N2O, molecular weight is 146.15, as common compound, the synthetic route is as follows.

b) (1S, 35)-N-(6-Fluoro-4-methylquinolin-2-yl)-N’-(imidazo [1, 2-a] pyridin-3- ylmethyl) cyclopentane-1, 3-diamine; (15, 3S)-N-(6-Fluoro-4-methylquinolin-2-yl) cyclopentane-1, 3-diamine (76 mg, 0.29 mmol) and imidazo [1, 2-a] pyridine-3-carbaldehyde (43 mg, 0.29 mmol) were dissolved in 2 mL of DCM and allowed to react for 4h. Sodium triacetoxyborohydride (112 mg, 0.53 mmol) was added and the mixture was stirred overnight. Much of the imine was left according to LC-MS. Sodium borohydride (50 mg, 1.3 mmol) was added and stirring was continued for 30 min. The mixture was acidified with 2M HCl and after 5 min the mixture was poured into water which was made alkaline with 2M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was chromatographed on a 2 g Isolute Si column with DCM/MeOH/TEA 100/5/1. Yield: 91 mg (77%). 1H NMR (400 MHz, CDCl3) 6 8.29 (m, 1H), 7.60 (dd, 1H), 7.56 (m, 1H), 7.46 (s, 1H), 7.31 (dd, 1H), 7.23 (m, 1H), 7.13 (m, 1H), 6.77 (m, 1H), 6.46 (s, 1H), 4.85 (bd, 1H), 4.44 (m, 1H), 4.03 (s, 2H), 3.29 (m, 1H), 2.44 (bd, 3H), 2.27 (m, 1H), 2.10-1. 95 (m, 2H), 1.77 (m, 1H), 1.55-1. 35 (m, 2H). 13C NMR (100 MHz, CDC13) 6 159.9, 157.5, 156.9, 147.0, 145.7, 145.12, 145.08, 133.1, 129.2, 129.1, 125.7, 124.9, 124.8, 124.7, 123.3, 119.3, 119.1, 118.5, 113.0, 112.8, 108.6, 108.4, 58.6, 52.3, 43.0, 41.5, 33.1, 32.7, 19.7. LC-MS [M+H] + 390.2.

The chemical industry reduces the impact on the environment during synthesis 6188-43-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
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. 851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-4-chloro-2-methoxypyridine

Into a 30 mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed 5-bromo-4-chloro-2-methoxypyridine (660 mg, 2.96 mmol, 1 eq), tert-butyl (2S)-2-methylpiperazine-l-carboxylate (1.2 g, 6 mmol, 2.02 eq), Pd2(dba) .CHCl (309 mg, 0.3 mmol, 0.10 eq), BINAP (372 mg, 0.60 mmol, 0.20 eq), t-BuONa (573 mg, 5.96 mmol, 2.01 eq) and toluene (4 mL). The resulting solution was stirred for 3 h at 95C in an oil bath. The crude mixture was concentrated and applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1 :3). This resulted in 180 mg (18%) of tert-butyl (2S)-4-(4-chloro-6- methoxypyridin-3-yl)-2-methylpiperazine-l-carboxylate as yellow oil. LCMS: m/z = 342 [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, 851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine.

Reference:
Patent; PIPELINE THERAPEUTICS, INC.; XIONG, Yifeng; SCHRADER, Thomas; CHEN, Austin; ROPPE, Jeffrey Roger; BACCEI, Jill Melissa; BRAVO, Yalda; (199 pag.)WO2019/241131; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, 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, Application In Synthesis of Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate

Example 1 2-({ [2-(2-methylbiphenyl-3-yl)imidazo[l,2-a]pyridin-6-yl]methyl}amino)ethanol Step 1: (2-bromoimidazo[l, To a solution of methyl 2-bromoimidazo[l,2-a]pyridine-6-carboxylate (200 mg, 0.784 mmol) (ArkPharm, catAK-31669) in tetrahydrofuran (5.0 mL) at 0 C was added 1.0 M diisobutylaluminum hydride in tetrahydrofuran (862 mu, 0.862 mmol). The resulting mixture was sitrred at room temperature for 1 h then it was quenched with saturated NH4CI aqueous solution (1 mL), stirred for 1 h then filtered through celite. The organic layer was dried over Na2S04, filtered and concentrated. The residue was used for next step without further purification. LC-MS calculated for C8H8BrN20 (M+H)+: m/z = 227.0; found 227.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; SHEN, Bo; LI, Jingwei; LI, Zhenwu; LIU, Kai; ZHANG, Fenglei; YAO, Wenqing; (120 pag.)WO2017/70089; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 887707-23-5, 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 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step B. 2-chloro-5-iodo-3-(trifluoromethyl)pyridine A suspension of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (3.0 g, 10.4 mmol) in POCI3 (8 mL) was heated at 100 C overnight. After cooling down to room temperature, the mixture was poured into ice (50 g). The resulting aqueous layer was neutralized by Na2C03 and extracted with EtOAc (70 mL x 2). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (100: 1-4: 1) as eluting solvents to afford 2- chloro-5-iodo-3-(trifluoromethyl)pyridine as a white solid (2.0 g, 63%). 1H NMR (500 MHz, CDC13) delta (ppm) 8.78 (d, / = 2.0 Hz, 1H), 8.28 (d, / = 2.0 Hz, 1H).

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 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine.

Reference:
Patent; BEAUFOUR-IPSEN (TIANJIN) PHARMACEUTICAL CO., LTD.; AUVIN, Serge; LANCO, Christophe; DUTRUEL, Oliver; CHAO, Qi; GU, Kaichun; WO2015/100617; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1532517-95-5, 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. 1532517-95-5, name is 5-Bromo-3-fluoro-2-nitropyridine, molecular formula is C5H2BrFN2O2, 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: [00441] Step 2. To a solution of 200b (450 mg, 2.0 mmol, 1.0 eq) in DMF (5 mL) were added TEA (400 mg, 4.0 mmol, 2.0 eq) and 3-fluoroazetidine (300 mg, 4.0 mmol, 2.0 eq) at rt. The mixture was stirred for 2 h under N2 at 90 C and then diluted with EtOAc (200 mL). The mixture was washed with brine (3×100 mL), dried over Na2S04 and concentrated to give black oil, which was purified by reversed phase HPLC (MeCN/H20 = 2: 1) to give 200c (300 mg, 53%) as yellow oil. ESI-MS (M+H)+: 276.0.

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 1532517-95-5, 5-Bromo-3-fluoro-2-nitropyridine.

Reference:
Patent; BIOGEN IDEC MA INC.; CHAO, Jianhua; ENYEDY, Istvan, J.; GUERTIN, Kevin; HUTCHINGS, Richard, H.; JONES, John, Howard; POWELL, Noel; VANVLOTEN, Kurt, D.; WO2014/8214; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 670253-37-9, 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 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

(Tsuruoka, A., et.al. ibid): Zinc cyanide (0.254 g, 2.17 mmol) and tetrakistriphenylphosphine palladium (0) (0.460 g, 0.394 mmol) were added to a solution of compound ii (1.00 g, 3.94 mmol) in NMP (10 mL). The reaction mixture was heated under N2(g) to 135C for 2 h, cooled to room temperature and partitioned between EtOAc (30 mL) and aqueous ammonia solution (0.35%, 50 mL). The organic fraction was separated, washed successively with water (2 x 100 mL) and brine (30 mL), dried (MgS04) and reduced in vacuo onto Si02. Column chromatography (Si02), eluting with 2: 1 Petrol-EtOAc to 1: 1 Petrol-EtOAc, afforded compound iii. (0.360 g, 2.35 mmol, 60%) as an off-white solid.

According to the analysis of related databases, 670253-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOTA EUROPE LTD; TYNDALL, Edward Malcolm; CZAPLEWSKI, Lloyd George; FISHWICK, Colin William Gordon; YULE, Ian Andrew; MITCHELL, Jeffrey Peter; ANDERSON, Kelly Helen; PITT, Gary Robert William; WO2013/91011; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem