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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., name: 3-Iodo-1H-pyrazolo[3,4-b]pyridine

Add 400 g (1.63 mol, 1.0 eq) of 3-iodo-1H-pyrazolo[3,4-b]pyridine, 369 g (1.96 mol, 1.2 eq) of o-fluorobenzyl bromide and 450 g (3.27 mol, 1.5 eq) of K2CO3 dissolved in 4L of DMF into a 5L 4-neck flask and react for 10 h at room temperature. Pour the reaction solution into water after thorough reaction as monitored by TLC, stir it to appear a plenty of grey solid, filter and recrystallize PE: EA=5:1 to obtain 411 g of light yellow solid. The yield is 71.16%. [0025] 11 H NMR (400 MHz, CDCl3) delta (ppm): 8.62 (d, 1H), 7.85 (d, 1H), 7.27 (dd, 1H), 7.11 (dd, 1H); 6.96-7.08 m, 3H), 5.82 (s, 2H).

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, 117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Pharmablock (Nanjing) R&D Co., Ltd.; Li, Jin; Yang, Xiaoyu; Zhu, Jingwei; Yang, Minmin; Wu, Xihan; US2014/309425; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, 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, Formula: C8H8ClNO, blongs to pyridine-derivatives compound. Formula: C8H8ClNO

A mixture of intermediate 4 (0.0003 mol) and 4-chloro-6,7-dihydro- 5H- cyclopenta[b]pyridin-7-ol (0.0003 mol) was stirred at 1500C for 20 minutes, cooled to room temperature, extracted with NaHCOs/DCM/methanol (few drops). The organic layers were combined, dried over MgSO4, filtered off and the solvent was evaporated. The residue (0.174g) was purified by column chromatography over silica gel (DCM/methanol 95/5, 93/7 to 90/1 ). The pure fraction was collected and the solvent was evaporated, yielding 0.097 g (68%) of compound 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37343; (2009); 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 174669-74-0, name is 2-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4FNO

Iodomethane 1.7 mL (27 mmol) and cesium carbonate 4.3 g (13. mmol) were added to a DMSO (20 mL) solution of 2-fluoropyridin-3-ol 1.0 g (8.8 mmol), and the mixture was stirred at 60C for 1 hour. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound 1.1 g (8.7 mmol, yield 99%) as a white solid. 1H-NMR spectrum (400MHz, DMSO-d6) delta:7.76 – 7.69 (m, 1H), 7.65 (ddd, J = 1.5, 8.0, 10.7 Hz, 1H), 7.31 (ddd, J = 0.9, 4.8, 8.0 Hz, 1H), 3.88 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 174669-74-0.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-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, Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

[Referential Example 13] Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxylate: 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (531 mg) was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at -78C, and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide into the reaction mixture at -78C for 1 hour, the mixture was warmed to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg) as a pale brown solid. 1H-NMR (DMSO-d6) delta: 2.37(3H,s), 2.64-2.77(4H,m), 3.54(2H,s) MS (FAB) m/z: 199(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1270557; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103-74-2, 2-(2-Hydroxyethyl)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, HPLC of Formula: C7H9NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9NO

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103-74-2, 2-(2-Hydroxyethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 106651-81-4 ,Some common heterocyclic compound, 106651-81-4, molecular formula is C7H9Cl2N, 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.

2-(2-Methoxycarbonylethyl)adenine (313 mg, 1.51 mmol) obtained by Reference example 22 and potassium carbonate (0.44 g, 3.18 mmol) were added to DMF (40 ml). The mixture was at 70C for 1 hour and then cooled to room temperature. Thereto was added 6-methyl-3-pyridylmethyl chloride hydrochloride (0.38 g, 2.13 mmol) and the mixture was stirred at room temperature for 15 hours. After removing the solvent, the residue was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (SiO2 20g, eluting solvent: CHCl3/MeOH = 100/1 ~ 30/ 1) to give the captioned compound (358 mg, 1.15 mmol) as a white solid.

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. 106651-81-4, 5-(Chloromethyl)-2-methylpyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1550662; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99163-12-9 ,Some common heterocyclic compound, 99163-12-9, molecular formula is C12H9NO, 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.

General procedure: Respective aromatic/hetro aromatic aldehydes (6a-r) (0.43 mmol) was added to a pre-mixed solution of compound 5 (0.43 mmol) in ethanol. The reaction content was refluxed for 0.5 h. The solids was filtered and rinsed with ethanol and dried to afford the respective hydrazone derivatives (7a-r) in 82-93 % yield (Scheme-I).

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. 99163-12-9, 4-Pyridin-4-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sree Lakshmana Rao; Basaveswara Rao, Mandava V.; Prasad; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 627 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89937-77-9, Methyl 1,2-dihydro-2-oxopyridine-4-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, 89937-77-9, blongs to pyridine-derivatives compound. Recommanded Product: 89937-77-9

LiH (78 mg) was suspended in DMF (5 ml), and a suspension of methyl-2-oxo-1,2-dihydropyridine-4-carboxylate (500 mg) in DMF (5 ml) was added dropwise thereto at room temperature. The suspension was stirred as it was, and a solution of 1-indo-2-methylpropane (506 mul) in DMF (5 ml) was added dropwise thereto over 10 min, followed by stirring at 50C for 15 hours. To the reaction solution was added 1M HCl at 0C, followed by extraction with EtOAc, and the organic layer was washed with saturated brine, dried over anhydrous MgSO4, and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:EtOAc=90:10 to 50:50) to obtain methyl-1-isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylate (440 mg) as white powders.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2003132; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 849020-87-7, 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.849020-87-7, name is 6-Hydroxy-4-(trifluoromethyl)nicotinic acid, molecular formula is C7H4F3NO3, molecular weight is 207.1068, as common compound, the synthetic route is as follows.

Diethyl chlorophosphate (0.045 ml, 0.312 mmol) was added to a solution of 6-hydroxy-4-(trifluoromethyl)nicotinic acid (0.065 g, 0.312 mmol) in pyridine, anhydrous (0.945 ml, 11.70 mmol) at room temperature under nitrogen. After stirring for lh, this solution was added to a vial containing 6-fluoro-4-(4- methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l, -biphenyl]-3-amine (step 3 from (a): 0.030 g, 0.078 mmol) under nitrogen and the reaction was heated to 70C for 3 hours. The pyridine was removed under reduced pressure and LCMS of the residue (dissolved in DCM, MeCN and MeOH) indicated complete conversion to the desired product. The mixture was loaded onto celite purified by flash chromatography [0.5-10% DCM/MeOH + 1% NH4OH] to methylpiperazin-1-yl)-3′-(mo holinomethyl)-[l,Gamma- biphenyl]-3-yl)-6-oxo-4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxarnide (0.024 g, 0.042 mmol, 53.6% yield) as a clear film. NMR (500 MHz, DMSO-d6) delta = 9.53 (s, 1H), 7.94 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.46 – 7.42 (m, 2H), 7.40 – 7.38 (m, 1H), 7.32 (d, J=7.3 Hz, 1H), 7.08 (d, J=12.5 Hz, 1H), 6.81 (s, 1H), 3.60 – 3.57 (m, 4H), 3.53 (s, 2H), 2.93 (br. s., 4H), 2.38 (br. s., 4H), 2.24 (s, 3H); LCMS [M+H]+ 574 g/mol.

The chemical industry reduces the impact on the environment during synthesis 849020-87-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-79-0, 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 69045-79-0, name is 2-Chloro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-1-(phenyl-3-boronic acid)-ethyl]-carbamic acid tert-butyl ester (1.29 g, 4.86 mmol) and 2-chloro-5-Iodo-pyridine (1.4 g, 11.4 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (4.75 g, 14.6 mmol) and water (5 mL). Argon was bubbled in to the above mixture for 10 min, and Pd(PPh3)4 (280 mg, 0.24 mmol) was added. The reaction mixture was stirred at 100 C. for 18 hand then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2¡Á100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (785 mg, 69%) as yellow oil. [0147] 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.8 Hz), 4.04 (q, 1 H, J=6.8 Hz), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.61 (d, 1H J =7.8 Hz,), 7.72 (s, 1H), 8.15 (dd, 1H, J=8.3, 2.5 Hz,), 8.73 (d, 1H, J=3.3 Hz).

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Yong-Jin; Sun, Li-Qiang; L’Heureux, Alexandre; US2004/110754; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem