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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: 1136-52-3

General procedure: A mixture of alpha4,3-O-isopropylidene pyridoxine, the respective saccharide and molecular sieves (4 A) was stirred under argon atmosphere in dry dichloromethane (5 mL) at rt for 1 h before it was cooled to 0 C. Silver triflate and N-iodosuccinimide (3.0 eq.) were added and the reaction mixture allowed to reach rt overnight. The mixture was diluted with dichloromethane (10 mL) and filtered through a pad of celite. Afterwards, the filtrate was washed with Na2S2O3 (10 % in water, 30 mL) and the aqueous phase was extracted with dichloromethane (3 x 40 mL). The combined organic layers were washed with distilled water (1 x 50 mL), brine (1 x 50 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product subjected to column chromatography using SiO2 (pentane/ethyl acetate 1/1 to 1/4, gradient elution) followed by C18 (methanol, isocratic) to afford the glycoside, which was used directly in the deprotection reaction.

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, 1136-52-3, (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol.

Reference:
Article; Bachmann, Thomas; Schnurr, Christian; Zainer, Laura; Rychlik, Michael; Carbohydrate Research; vol. 489; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1824-81-3, 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. 1824-81-3, name is 2-Amino-6-picoline. A new synthetic method of this compound is introduced below.

2. Dissolve 10.80 g of 2-amino-6-methylpyridine (Compound 9) in 500 mL of acetonitrile, add 33.7 g of N-iodosuccinimide, and react at room temperature for 3 h. The precipitate was filtered, washed with 200 mL of cold acetonitrile, and dried under vacuum to obtain 12.2 g (compound 10) as an off-white solid with a yield of about 52%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1824-81-3, 2-Amino-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; China Agricultural University; Wang Zhanhui; Shen Jianzhong; Wen Kai; Li Chenglong; Yu Xuezhi; Zhang Suxia; Shi Weimin; Yu Wenbo; (19 pag.)CN110713457; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1149-23-1, 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 1149-23-1, name is Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of HEH or BNAH (0.1 mmol) in ethanol or acetonitrile (2 mL) wasadded polysulfide 1 (0.2 mmol). The solution was incubated at r.t. or 37 C for 20 h(for HEH) or 5 h (for BNAH) under dark. After removing the solvent under reducedpressure, the yield of product 2 or 3 were determined by 1H-NMR.

According to the analysis of related databases, 1149-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Peng, Bo; Liu, Chunrong; Li, Zhen; Day, Jacob J.; Lu, Yun; Lefer, David J.; Xian, Ming; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 542 – 545;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6188-23-4 , The common heterocyclic compound, 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, 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.

Step: 1 To a solution of 6-bromoimidazo [l ,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[l,2- ajpyridine (22 g, 67%) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 8.29 (s, 1H), 7.58 (d, J= 9.2 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 7.27 (s, 1H).

The synthetic route of 6188-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113118-83-5, 5-Methoxynicotinaldehyde, 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, Product Details of 113118-83-5, blongs to pyridine-derivatives compound. Product Details of 113118-83-5

A 250 mL round bottom flask equipped with a magnetic stirring bar, nitrogen inlet, and septum was charged with THF (100 mL) and butyllithium (7.29 mL, 18.23 mmol). After cooling to -78C, 2-(naphthalen-2-yl)acetonitrile (3.05 g, 18.23 mmol) was added, and after 60 minutes, 5-methoxynicotinaldehyde (2.5 g, 18.23 mmol) was added via syringe. After stirring at (-78C) for 3 hours, the reaction was quenched by the addition of acetic acid (2.1 mL) while stirring at -70C. The aqueous layer was extracted with Et20 (2 x 250 mL), and the combined organic extracts were washed with brine (250 mL) and dried (MgSC^). The material was concentrated in vacuo to give a crude aldol (6 g). ISCO purification on silica gel eluting with 0-100% of ethyl acetate in hexane afforded the product as an antv.syn mixture (4 g, 72%). 1H NMR (500 MHz, CDCk) delta 2.80 (d, J=3.7 Hz, 1 H), 3.78 (s, 3 H), 4.24 (d, J=5.2 Hz, 1 H), 5.12 (d, J=3.4 Hz, 1 H), 7.18 – 7.38 (m, 4 H), 7.47 – 7.61 (m, 2 H), 7.73 – 7.93 (m, 5 H), 8.04 (d, J=1.5 Hz, 1 H), 8.23 (d, J=2.7 Hz, 1 H).

The synthetic route of 113118-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; RICHELSON, Elliott; FAUQ, Abdul H.; CARLIER, Paul R.; MONCEAUX, Christopher J.; WO2014/159251; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73027-79-9, 4,6-Dichloronicotinic acid, 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, SDS of cas: 73027-79-9, blongs to pyridine-derivatives compound. SDS of cas: 73027-79-9

4,6-Dichloro-N-(2-hydroxyethyl’)-N-methylpyridine-3-carboxamide,cKpgammacl oOxalyl chloride (1.12 mL, 12.50 mmol), followed by DMF (2 drops), were added to a mixture of 4,6-dichloronicotinic acid (2g, 10.42 mmol) in 4M HCl in dioxane (2.62 mL, 10.42 mmol) and DCM (40 mL). The reaction was stirred at RT for 2 hours, the volatiles removed in vacuo and the residue dissolved in DCM (20 mL). The solution was added dropwise to a mixture of 2-(methylamino)ethanol (0.93 mL, 11.46 mmol) and triethylamine (3.2 mL, 22.92 mmol) in DCM (20 mL) and the mixture stirred at RT for 20 hours. The mixture was concentrated in vacuo and ethyl acetate (100 mL) added to the residue. The organics were washed with water (100 mL), saturated sodium bicarbonate solution (50 mL), brine (50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil. The residue was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (1.8 g). 1E NuMR delta (CDCl3): 2.90 & 3.11 (2xs, 3H), 3.17 – 3.91 (m, 4H), 7.35 – 7.40 (m, IH), 8.28 – 8.33 (m, IH); m/z 249 (M+H)+; The hydroxyl-containing compounds used in the synthesis of Examples 2a-2c were prepared in an analogous fashion from 2-(methylamino)ethanol and the appropriate carboxylic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73027-79-9, 4,6-Dichloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7040; (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. 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. COA of Formula: C10H9BrN2O2

Ethyl 5 -bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (0.100 g, 0.372 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (0.101 g, 0.483mmol) and XPhos-Pd G3 (7.9 mg, 9.3 jimol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuumlAr), then THF (2 mL) and potassium phosphate tribasic (0.5 M aq.) (1.12 mL, 0.557 mmol) were added. The reaction mixture was degassed again, and stirred at 100 C for 1 h. Solvent was removed under reduced pressure. The obtained residue was dissolved in MeOH (1.0 mL)/THF (1.0 mL), and LiOH (1 M aq.) (1 .12 mL, 1.12 mmol) was added. The reaction mixture was stirred under microwave irradiation at 120 C for 15 mm. The mixture was acidified with TFA, the solvent was removed under reduced pressure, the residue was purified by preparativeHPLC to afford Intermediate 39 (0.055 g, 61% yield) as an off-white solid. MS(ESI) m/z:243.0 (M+H) ?H NMR (500MHz, DMSO-d6) oe ppm 8.81 (dd, J=7.2, 0.8 Hz, 1H), 8.43(s, 1H), 8.33 (s, 1H), 8.10 (dd,J=1.9, 0.8 Hz, 1H), 8.05 (s, 1H), 7.36 (dd,J=7.3, 2.1 Hz,1H), 3.90 (s, 3H).

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, 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 929617-35-6, 5-Bromo-1H-pyrazolo[3,4-c]pyridine, 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, COA of Formula: C6H4BrN3, blongs to pyridine-derivatives compound. COA of Formula: C6H4BrN3

General procedure: To a stirred solution of 5-bromo-1W-pyrazolo[3,4-c]pyridine (1 g, 5.07 mmol) in DMF (10mL), 60% NaH (0.405 g, 10.14 mmol) was added at 0C and it was stirred at RT for 30 min. Then, (bromomethyl)cyclobutane (1.12 g, 7.56 mmol) was added to the mixture at 0 C and it was stirred at RT for 16 h. The reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with brine (20 ml). The combined organic layers were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The crude compound was purified by column chromatography using 10% EtOAc/pet ether as eluent to afford fraction-1 5-bromo-1-(cyclobutylmethyl)-1H-pyrazolo[3,4-c]pyridine (reference example 6) (500 mg) as an off-white solid, and 20% EtOAc/pet ether as eluent to afford fraction-2 5- bromo-2-(cyclobutylmethyl)-2W-pyrazolo[3,4-c]pyridine (reference example 7) (450 mg) as an off-white solid Reference example 6: LC-MS (method 1): Rt = 2.30 min; m/z = 265.86 (M+H+). Reference example 7: LC-MS (method 1): Rt = 2.06 min; m/z = 265.61 (M+H+).

The synthetic route of 929617-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 375368-83-5, Adding some certain compound to certain chemical reactions, such as: 375368-83-5, name is 3-Bromo-6-fluoro-2-methylpyridine,molecular formula is C6H5BrFN, 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 375368-83-5.

Step A. 5-bromo-6-methylpyridin-2-ol 3-Bromo-6-fluoro-2-methylpyridine (5 g, 0.021 mol) was added into HQ (6mol/L, 40mL), and the mixture was stirred, and refluxed for 2 hours. The product was detected by TLC. After the reaction was finished, the mixture was quenched with saturated aqueous NaHC(, filtered, and concentrated to afford the title compound.

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. 375368-83-5, 3-Bromo-6-fluoro-2-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); 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. 6937-03-7, name is Methyl 2-aminoisonicotinate, molecular formula is C7H8N2O2, 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. name: Methyl 2-aminoisonicotinate

To solution of (2,4-dichloro-phenoxyacetic acid (0.200 g, 0.9 mmol), 2-amino isonicotinic acid methyl ester (207 mg, 1.36 mmol) and DMAP (0.222 g, 1.81 mmol) in DMF 13 mL was added PyBOP (946 mg, 1.81 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9-4:6) to give 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.229 g, 71% yield). 1H NMR (DMSO-d6, 300 MHz) 10.87 (1H, s, CONH), 8.53 (2H, d, J=4.8 Hz, pyridine), 7.58 (m, 2H, aromatic), 7.35 (1H, dd, J=1.8&9.0 Hz, pyridine), 7.11 (1H, d, J=8.4 Hz, aromatic), 4.98 (2H, s, OCH2), 3.88 (3H, s, OCH3).

With the rapid development of chemical substances, we look forward to future research findings about 6937-03-7.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem