Category: 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.100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine, molecular formula is C6H6BrN3O2, molecular weight is 232.04, as common compound, the synthetic route is as follows.name: 2-Amino-5-bromo-4-methyl-3-nitropyridine

This reaction was conducted under inert gas protection. The reaction vessel was first charged with 2000 ml methanol and cooled to about 0 C. with slight agitation. Then 9.1 kg acetyl chloride was added. The exothermic reaction was then cooled and agitated for 10 minutes. The next addition was 100 g 2-amino-5-bromo-3-nitro-4-picoline (the compound of formula 2 at 0 C. Then 236.5 g of t-butyl nitrite was added at a rate such that the temperature did not exceed 5 C. The slight evolution of nitrogen gas was noted. After the completion of the reaction, cooling was removed and the reaction mixture within the vessel was allowed to warm to 25 C. in about 30 minutes. The mixture was agitated at 25 C. for about 3-4 hours. After 4-5 hours a clear solution was obtained. Reaction completeness was monitored by HPLC after about 4 hours. The reaction was complete after about 5 hours. The reaction mixture was concentrated in vacuo to about 1000 mL. Then 500 ml of water was added and the product precipitated. Then 250 ml saturated sodium bicarbonate solution was added with good agitation to neutralize the HCl and dissolve the hydroxy impurity. The mixture was agitated at 20-25 C. for about 15 minutes and then the precipitate was collected and washed with 1000 ml of water. The product was then dried at 40 C. in vacuo. Yield was 75.0 g. Analytical data: m.p. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (DMSO-d6) (delta, ppm): 2.31 (s, 3H), 3.96 (s, 3H), 8.55 (s, 1H): 13C-NMR (DMSO-d6) (delta, ppm): 17.49, 54.91, 99.41, 114.39, 141.02, 149.23, 153.46; HRMS calcd for C7H7BrN2O3 245.96401 found (M+1): 246.97184; Elemental Analysis: calcd for C7H7BrN2O3: C 34.03, H 2.85, N 11.34; found: C 33.81, H 2.91, N 11.24.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Liu, Wansheng; Patel, Sunil S.; Cuniere, Nicolas; Lear, Yvonne; Deshpande, Prashant P.; Simon, Jeffrey N.; Lai, Chiajen; Pullockaran, Annie J.; Soundararajan, Nachimuthu; Bien, Jeffrey T.; US2007/32503; (2007); 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. 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H7Br2NO

a) Preparation of Intermediate 24; A mixture of 2-bromo-1-(4-pyridinyl)-ethanone, hydrobromide (0.02 mol) and (5-chloro-2,4-dimethoxyphenyl)-thiourea (0.02 mol) in EtOH (200 ml) was stirred and refluxed for 4 hours, then cooled to room temperature. The resulting precipitate was filtered off, washed with EtOH and dried, yielding 6.0 g (60%) of intermediate 24 as a hydrobromide salt (.HBr).

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, 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; Thuring, Johannes Wilhelmus John F.; MacDonald, Gregor James; Grantham, Christopher James; Dinklo, Theodorus; Lesage, Anne Simone Josephine; US2011/269748; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 159451-66-8, Adding some certain compound to certain chemical reactions, such as: 159451-66-8, name is N-Boc-2-Amino-5-bromopyridine,molecular formula is C10H13BrN2O2, 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 159451-66-8.

(VI) Scheme VI: Intermediate 41: tert-butyl (5-(1-((1s,4s)-4-hydroxycyclohexyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)pyridin-2-yl)carbamate Under the protection of nitrogen, 0.218 g (0.8 mmol) of tert-butyl 2-carbamate -5-bromopyridine (Intermediate 38), 0.244 g (0.96 mmol) of bis(pinacolato)diboron, 0.234 g (2.4 mmol) of potassium acetate and 0.052 g (0.064 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride were suspended in 15 ml of dioxane, and heated at 100 C for 2 h. The reaction was monitored by TLC. After the reaction was completed, the crude reaction solution was cooled to room temperature, added with 0.2 g (0.54 mmol) of Intermediate 40, 0.9 g (2.7 mmol) of cesium carbonate, 10 ml of dioxane, 10 ml of 2M sodium carbonate solution and 0.044 g (0.054 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride, and heated at 110 C for 5 h. The reaction was monitored by TLC. After the reaction was completed, most of dioxane was removed from the reaction solution, and the residue was added with water and extracted with dichloromethane. The organic phases were combined, dried, and rotary evaporated to dryness to afford a crude product. The crude product was purified by preparative silica gel plate (dichloromethane/methanol =10/1, V/V) to afford a product (240 mg) as a reddish brown solid. Yield: 90.9%.

According to the analysis of related databases, 159451-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Forelandpharma Co. Ltd.; ZHANG, Xingmin; JI, Qi; WANG, Lei; GAO, Congmin; WANG, Ensi; DU, Zhenjian; GONG, Longlong; CHEN, Bo; (137 pag.)EP3072893; (2016); 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 131747-60-9, name is (2-Fluoropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6FNO

c Preparation of 2-fluoropyridine-4-carbaldehyde: A solution of 5 g (39 mmol) of (2-fluoropyridin-4-yl)methanol in dichloromethane was added dropwise to a solution of 4.6 ml (54 mmol) of oxalyl chloride and 7.6 ml (106 mmol) of dimethyl sulfoxide (DMSO) in 450 ml of dichloromethane at -78 C. and the mixture was stirred for 15 minutes. 24 ml (180 mmol) of triethylamine were then added and the reaction solution was slowly warmed to RT. It was poured onto 500 ml of water and washed once each with 10% strength citric acid (200 ml) and 10% strength sodium carbonate solution. The dichloromethane phase was dried over magnesium sulfate and concentrated under reduced pressure. Yield: 4.60 g (37 mmol), 94%.

With the rapid development of chemical substances, we look forward to future research findings about 131747-60-9.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US6358978; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139042-59-4, 5-Acetyl-2-bromopyridine, 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, name: 5-Acetyl-2-bromopyridine, blongs to pyridine-derivatives compound. name: 5-Acetyl-2-bromopyridine

The mixture of compound 34-1 (25 g, 125.6 mmol), NBS (24.5 g. 138.2 mmol) and / TSA (3.4 g, 20.9 mmol) was stirred at 100 C for 2 hrs under N2. After the reaction was completed, the mixture was cooled to rt. and 200 mL of DCM was added. The organic layer were washed with water (50 mL x 3) and brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1 ) to give the title compound as yellow slurry (25 g, 71 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 279.9 [M+H] +; NMR (400 MHz, CDC13) delta (ppm): 8.95 (d, 1 H, J = 1.12 Hz), 8.1 1-8.14 (m, 1H), 7.66-7.68 (m, 1H), 4.41 (s, 2H).

The synthetic route of 139042-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; TAN, Yumei; LUO, Huichao; WO2014/19344; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 64119-42-2, 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 64119-42-2, name is Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

(a) 1-[3-Cyano-5-(ethoxycarbonyl)-6-methylpyridine-2-yl]azetidine-3-carboxylic acid Ethyl 6-chloro-5-cyano-2-methylnicotinate (50.98 g, 227 mmol), azetidine-3-carboxylic acid (24.09 g, 238 mmol) and DIPEA (118.9 mL, 681 mmol) were suspended in EtOH (250 mL) and heated at reflux for 1 h. The reaction mixture was cooled to r.t and added drop-wise to KHSO4 (154.5 g, 1135 mmol) in water (3000 mL). The solids were collected by filtration and dried under vacuum to afford 1-[3-Cyano-5-(ethoxycarbonyl)-6-methylpyridine-2-yl]azetidine-3-carboxylic acid as a solid, which was used without further purification. Yield: 65.33 g (100%). 1H NMR (400 MHz, CDCl3): delta 1.37 (3H, t, J=7.1 Hz), 2.72 (3H, s), 3.59-3.68 (1H, m), 4.31 (2H, q, J=7.1 Hz), 4.55-4.68 (4H, m), 8.28 (1H, s). MS m/z: 290 (M+1).

According to the analysis of related databases, 64119-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2007/244088; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235865-75-4, 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 1235865-75-4, name is Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate. This compound has unique chemical properties. The synthetic route is as follows.

Example 11 methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoate A mixture of EXAMPLE 1H (1.55 g), EXAMPLE 1E (2.42 g), and HK2PO4 (1.42 g) in dimethylsulfoxide (20 mL) at 135 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (400 mL), and washed three times with 1M aqueous NaOH, and brine, and concentrated. The crude product was chromatographed on silica gel with 10-50% ethyl acetate/hexanes.

According to the analysis of related databases, 1235865-75-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tao, Zhi-Fu; Wang, Xilu; Wendt, Michael; Souers, Andrew; Judd, Andrew; Kunzer, Aaron; Sullivan, Gerard; US2014/275082; (2014); 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. 517918-95-5, name is 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, molecular formula is C8H5N3, 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. Product Details of 517918-95-5

The compound obtained from Preparation Example 121 was dissolved in ethanol (100ml), and 6N sodium hydroxide (17ml, 102mmol) was added thereto. The mixture was stirred for 3 days at 100 and then distilled under reduced pressure. 1 N hydrochloride solution was added and the residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and the residue was dissolved in tetrahydrofuran (400ml). 0.25M solution of diazomethane in diethyl ether (30ml, 7.5mmol) was slowly added dropwise. The mixture was stirred for 30 minutes at 0 and then distilled under reduced pressure to obtain the title compound (1.2g, 67%).

With the rapid development of chemical substances, we look forward to future research findings about 517918-95-5.

Reference:
Patent; LG LIFE SCIENCES LTD.; LEE, Sung Bae; PAEK, Seung Yup; YOON, Sook Kyung; YOON, Seung Hyun; CHOI, Jeung Soon; WO2014/73904; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 154078-83-8, Adding some certain compound to certain chemical reactions, such as: 154078-83-8, name is Ethyl 2-(3-nitropyridin-2-yl)acetate,molecular formula is C9H10N2O4, 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 154078-83-8.

H) ethyl (3-aminopyridin-2-yl)acetate A mixture of ethyl (3-nitropyridin-2-yl)acetate (29.0 g) and 10% palladium-carbon (containing water (50%), 2.90 g) in ethanol (400 mL) was stirred under a hydrogen atmosphere (50 psi) at room temperature for 3 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (25.5 g). 1H NMR (400 MHz, CDCl3) delta 1.26 (3H, t, J=7.2 Hz), 3.85 (2H, s), 4.17 (2H, q, J=7.2 Hz), 4.32 (2H, br s), 6.99-7.06 (2H, m), 7.99-8.01 (1H, m).

According to the analysis of related databases, 154078-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Kawasaki, Masanori; Mikami, Satoshi; Nakamura, Shinji; Negoro, Nobuyuki; Ikeda, Shuhei; Nomura, Izumi; Ashizawa, Tomoko; Imaeda, Toshihiro; Seto, Masaki; Sasaki, Shigekazu; Marui, Shogo; Taniguchi, Takahiko; (130 pag.)US2016/159808; (2016); 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.944401-77-8, name is 2-Amino-4-fluoropyridine, molecular formula is C5H5FN2, molecular weight is 112.105, as common compound, the synthetic route is as follows.Safety of 2-Amino-4-fluoropyridine

To a solution of 2-amino-4-fluoropyridine (75.0 g, 0.67 mol) in dry acetonitrile (700 mL), N-bromosuccinimide (122.8 g, 0.69 mol) was added portion wise upon stirring and cooling in an ice-water bath. The reaction mixture was stirred at r.t. for 1 h. After evaporation under reduced pressure, the residue was thoroughly washed with water (3 x 300 mL), taken up by acetonitrile and evaporated under vacuum yielding the title compound as an off white solid (124 g, 97 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944401-77-8, 2-Amino-4-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BROWN, Julien Alistair; DELIGNY, Michael; HEER, Jag Paul; JACKSON, Victoria Elizabeth; JADOT, Sophie; KROEPLIEN, Boris; MAC COSS, Malcolm; SABNIS, Yogesh Anil; SWINNEN, Dominique Louis Leon; VAN HOUTVIN, Nathalie; ZHU, Zhaoning; WO2015/86527; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem