Category: pyridine-derivatives

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. 6265-73-2, name is N-(2-Hydroxyethyl)nicotinamide. A new synthetic method of this compound is introduced below., Safety of N-(2-Hydroxyethyl)nicotinamide

General procedure: A4 (100mg, 0.6mmol) was combined with 2-chloro-4-nitrophenyl isothiocyanate (129mg, 0.6mmol) in anhydrous THF (30mL) at 0C, followed by the addition of DBU (106mg, 0.7mmol). The resultant mixture was stirred at 0C for 20min, after which the ice bath was removed, and the reaction mixture was stirred at room temperature until the completion of the reaction indicated by TLC. The crude product was purified by column chromatography (chloroform/methanol, 30/1).

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, 6265-73-2, N-(2-Hydroxyethyl)nicotinamide.

Reference:
Article; Bai, Zhongjie; Zhang, Jinlong; Zhang, Qiuping; Wang; Li, Jili; Zhao, Quanyi; Wang, Zhen; He, Dian; Zhang, Jingke; Liu, Bin; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3307 – 3318;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 21427-62-3 ,Some common heterocyclic compound, 21427-62-3, molecular formula is C5H2Cl2N2O2, 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.

Example 10; (+/-)-9-[Acetyl-(3,5-bis-trifluoromethylbenzyl)amino]-3-chloro-2-methoxy-6,7,8,9- tetrahydro-pyrido[3,2-b]azepine-5-carboxylic acid isopropyl ester; Step 1;. Preparation of 5-Chloro-3-nitro-pyridine-2-carbonitrile; Add 3-nitro-5-chloro-pyridin-2-ol (3.9 g, 22.3 mmol) to a mixture of phosphorous oxychloride (4.17 mL) and dimethylformamide (10 mL). Heat the resulting mixture at 110 C for 30 min. Cool the reaction mixture to room temperature and pour onto ice- water. Add sodium bicarbonate slowly until neutralization occurs and extract with ethyl acetate. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Dissolve the residue in N-methyl pyrrolidinone (4 mL), add copper (I) cyanide (2.39 g, 26.7 mmol) and heat at 160 C for 15 min. Cool the reaction mixture to room temperature and pour onto ice water and ethyl acet ate. Add a saturated solution of sodium bicarbonate, separate the organic layer, and extract the aqueous layer with ethyl acetate. Dry the combined organic layers over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue using silica gel chromatography, eluting with ethyl acetate/hexanes 1: 3 to afford the title cornpound (1.01 g, 26%). H-NMR (CDC13, 300 MHz) : No. 8.61 (s, 1H), 8.95 (s, 1H).

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. 21427-62-3, 2,5-Dichloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); 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 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Safety of tert-Butyl (6-chloropyridin-3-yl)carbamate

1,1-Dimethylethyl (6-Chloro-4-iodo-3-pyridinyl)carbamate n-Butyllithium (1.6M in hexanes, 22 mL, 35 mmol) was added dropwise to a stirred, cooled (-78 C.) solution of 1,1-dimethylethyl (6-chloro-3-pyridinyl)carbamate (Description 6, 2.68 g, 11.7 mmol) and N,N,N’,N’-tetramethylethylenediamine (5.3 mL, 4.1 g, 35 mmol) in ether (60 mL). The mixture was allowed to warm to -10 C. and stirred for 2 h. The mixture was cooled to -78 C. and a cooled (-10 C.) solution of iodine (6.0 g, 24 mmol) in ether (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 18 h. Saturated aqueous ammonium chloride was added and the mixture was extracted with ether. The combined organic fractions were washed with aqueous sodium metabisulfite (10%), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as a brown solid (2.3 g, 55%). 1H NMR (400 MHz, CDCl3) delta 8.94 (1H, s), 7.73 (1H, s), 6.64 (1H, br s), and 1.54 (9H, s).

With the rapid development of chemical substances, we look forward to future research findings about 171178-45-3.

Reference:
Patent; Dinnell, Kevin; Elliott, Jason Matthew; Hollingworth, Gregory John; Shaw, Duncan Edward; US2002/22624; (2002); 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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, 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 15862-37-0

A 150 mL pressure flask was charged with (6-chloro-2-methoxypyridin-3- yl)boronic acid (2.5 g, 13.3 mmol) and 2,5-dibromo-3-nitropyridine (3.38 g, 12.01 mmol). The solids were suspended in THF (60 mL). The mixture was treated with PdCl2(dppf)-CH2Cl2 adduct (0.545 g, 0.667 mmol) and K3P04 (2M, 20 mL, 40 mmol). Argon was bubbled through the mixture for 5 min while sonicating. The flask was capped and heated to 80C in a preheated oil bath. The reaction was cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to remove THF. The remaining water layer was diluted further with water and was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered and concentrated under vacuum to give a solid. The material was taken up in DCM and a minimum of ethyl acetate and purified by flash column chromatography (80g ISCO column, 0-30% ethyl acetate/hexanes over 600 mL, then 50-100% over 300 mL). Like fractions were concentrated to give 4.5g (78%). NMR (400MHz, CDCh) delta 8.94 (d, J=2.0 Hz, 1H), 8.44 (d, J=2.0 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 3.89 (s, 3H). LC/MS (M+H) = 345.95

With the rapid development of chemical substances, we look forward to future research findings about 15862-37-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 29681-38-7, Methyl 5-methylpicolinate, 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, 29681-38-7, blongs to pyridine-derivatives compound. Safety of Methyl 5-methylpicolinate

Example 8. Synthesis of 1-548-101. Into a 2000-mL 4-necked round-bottom flask, was placed a solution of methyl 5-methylpicolinate (85 g, 539.68 mmol, 1.00 equiv, 96%) in CC14 (1000 mL), N-bromosuccinimide (1 10 g, 617.98 mmol, 1.10 equiv), and benzoyl peroxide (3.5 g, 14.45 mmol, 0.03 equiv). The resulting solution was heated to reflux overnight. The solids were removed by filtration. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :30-l :5). This resulted in 15 g (1 1%) of methyl 5-(bromomethyl)picolinate as a light-yellow solid.LC-MS: (ES, m/z): 232 [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,29681-38-7, its application will become more common.

Reference:
Patent; MERIAL LIMITED; MENG, Charles, Q.; MURRAY, Clare, Louise; BLUHN-CHERTUDI, Itta; SOUKRI, Mustapha; WO2013/3505; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54916-66-4, 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 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

As shown in step 4(b)-i of Scheme 4(b), HATU (8.194 g, 2.55 mmol) and DIPEA (5.570g, 7.507 mL, 43.10 mmol) was added to a solution of 5-bromo-2-methoxypyridine-3- carboxylic acid (5 g, 21.55 mmol) in DMF (50 mL). The resulting solution was stirred for 10 minutes followed by the addition of ethanamine hydrochloric acid (1.757 g, 2.196 mL, 21.55 mmol). The resulting solution was stirred at room temperature for 5 hours. To the reaction mixture was added water (100 mL) and ethyl acetate (100 mL). The organic layer was separated and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-2% methanol in dichloromethane gradient) to produce 5-bromo-N-ethyl-2-methoxynicotinamide as off white solid (Compound 2015, 3.4g): 1H NMR (DMSO-d6) delta 8.41 (d, J = 2.5 Hz, 1H), 8.31 (s, 1H), 8.20-8.13 (m, 1H), 3.95 (s, 3H), 3.35-3.23 (m, 2H), 1.11 (t, J = 7.2 Hz, 3H).

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

3.68. Compound 69: (lR,2R)-N-( 6-(2-ethyl-4-fluorophenox )-l-methyl-lH-imidazo[4, 5-c]pyridin-4- 3.68.1. Step i: 2,6-dichloro-N-methylpyridin-4-amine 33% v/v MeNH2 solution in EtOH (101 mL) is added dropwise to a suspension of 2,4,6- trichloropyridine (25 g) in EtOH (25 mL). The mixture is stirred at room temperature for 24 h. The mixture is concentrated and the residue is treated with DIPE. The precipitated desired product is filtered off and dried under vacuum.

According to the analysis of related databases, 16063-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); 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. 1312784-89-6, name is tert-Butyl 1-methyl-6,7-dihydro-1H-imidazo[4,5-c]pyridine-5(4H)-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 1312784-89-6

Under nitrogen protection, dissolve 5.0Kg of 1-methyl-6,7-dihydro-1H-imidazo [4,5-C] pyridine-5- (4H) -carboxylic acid tert-butyl ester in 30L of tetrahydrofuran and stir, The temperature of the dry ice ethanol bath is reduced to -60 ,Slowly add 16.9L n-butyl lithium n-hexane solution (2.5mol / L),Control the reaction temperature not to exceed -50 C, keep the temperature at -50 C ~ -60 C for 1 hour after the addition is completed, pass in 2.8 kg of dried carbon dioxide gas, keep the temperature not to exceed -40 C, and increase the temperature to 20 after completion Reaction at -25 C for 2 hours; add 1mol / L dilute hydrochloric acid aqueous solution to adjust PH = 2-3, stir for 10 minutes, separate layers, extract the aqueous layer with 80L ethyl acetate, combine the organic layers, wash with 30L saturated brine, without Dry over sodium sulfate, filter and concentrate to give an oily liquid 1-methyl-6,7-dihydro-1H-imidazo [4,5-C] pyridine-5- (4H) -carboxylic acid tert-butyl ester-2- Carboxylic acid 5.2Kg, purity by HPLC detection was 98.2%, yield was 87.7%.

The synthetic route of 1312784-89-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Gao Jian; Yu Jurong; (8 pag.)CN110950886; (2020); A;,
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 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

A colorless mixture of A-13 (900.0 mg, 3.34 mmol) in H2504 (50%,10.0 mL) was stirred at 120 C for 3 hours. The mixture was diluted with ice-water, neutralizedwith solid Na2CO3 to pH = 7, and extracted with DCM (50 mL x 2). The combined organiclayers were washed with brine (10 mL), dried over Na2504, filtered and concentrated to affordA-14 (550.00 mg, 2.79 mmol) as an oil. ?H NMR (400 MHz, CDC13) oe11 8.38 – 8.32 (m, 1H),7.95 (d, 1H), 7.72 (d, 1H), 6.83 (dd, 1H), 6.47 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 885276-93-7.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5409-39-2, 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. 5409-39-2, name is 5-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

To a solution of intermediate 32a (10.0 g, 57.6 mmol) in HBr [(31.0 mL (100%), 286.4 mmol)] at 0 00, sodium nitrite (13.8 g, 199.9 mmol) was added drop wise. To the stirred solution Br2 (10.0 mL, 197.1 mmol)in water was added and stirred at roomtemperature for 1 h. The reaction mixture was basified with NaHCO3 solution (PH=7) and extracted with ethyl acetate, washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo to yield the title product (10.0 g, 73.0%) as a yellow solid.

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 5409-39-2, 5-Chloro-3-nitropyridin-2-amine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202528; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem