Category: pyridine-derivatives

Reference of 10201-71-5, Adding some certain compound to certain chemical reactions, such as: 10201-71-5, name is 2-Amino-3-methoxypyridine,molecular formula is C6H8N2O, 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 10201-71-5.

EXAMPLE 2 (endo)-N-(8-Methyl-8-azabicyclo[3,2,1]oct-3-yl)-N’-(3-methoxy-pyrid-2-yl)urea (E2) STR13 A solution of 2-amino-3-methoxypyridine (0.55 g) and 1,1′-carbonyldiimidazole (0.86 g) in xylene (50 ml) was stirred at room temperature for 1 h. A solution of (endo)-8-methyl-8-azabicyclo[3,2,1]octan-3-amine (0.8 g) in xylene (10 ml) was added and the whole heated to reflux for 2 h. The reaction mixture was evaporated to dryness and the residue partitioned between CHCl3 (100 ml) and saturated NaHCO3 solution (50 ml). The CHCl3 extract was removed, dried (K2 CO3) and evaporated to dryness. The residue was purified by column chromatography (Al2 O3, CH2 Cl2 -CHCl3), to give the title compound (0.9 g) m.p. 178-80.

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. 10201-71-5, 2-Amino-3-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beecham Group, p.l.c.; US4808588; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14237-71-9, 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 14237-71-9, name is 2-Chloro-4,6-dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

2-chloro-4,6-dimethyl-nicotinonitrile (2.5 g, 15.01 mmol) was dissolved in anhydrous methanol (70mL), added with sodium methoxide (4. 27 g, 75.03 mmol) at 0 C and stirred for about 10 hours at nitrogen atmosphere. The above mixture was concentrated under reduced pressure and then neutrailized with a saturated solution of ammonium chloride and then extracted twice with 150 mL of methylenechloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (20% EtOAc/Hexanes) was performed on the resulting residue and 2.41g (99%) of 2- methoxy-4, 6-dimethyl-nicotinonitrile was obtained in white solid. ‘H NMR (300 MHz, CDC13) 8 2.44 (s, 3H), 2.45 (s, 3H), 4.01 (s, 3H), 6.68 (s, 1H).

According to the analysis of related databases, 14237-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); 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. 108130-10-5, name is Ethyl 2,6-dichloro-4-methylnicotinate, the common compound, a new synthetic route is introduced below. Product Details of 108130-10-5

a) Synthesis of 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester A mixture of 8.2 g (35.0 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid ethylester, 3.7 ml (43.8 mmol) N-methylethylamine and 8.9 ml (52.5 mmol) DIPEA in NMP (25 ml) was heated in the MW to 90 C. for 1 h. Then the solution was diluted with water, a 1M aq. NaOH sol. and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 4.0 g (15.6 mmol, 44%) 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester.

The synthetic route of 108130-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2012/101079; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-12-1 , The common heterocyclic compound, 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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 12 Preparation of Compound 7 (0241) (0242) To a 0 C. solution of 5-chloro-3-hydroxypyridine (3.00 g, 23.16 mmol) in tetrahydrofuran (90 mL) was added lithium tert-butoxide (1.0 M in THF, 23.16 ml, 23.16 mmol) dropwise, so as to maintain the internal reaction temperature below 10 C. (0243) In a separate flask, compound 12a (10.0 g, 22.1 mmol) was dissolved in tetrahydrofuran (50.0 mL). This solution was added dropwise to the lithium phenoxide solution over 2 min below 10 C. The cooling bath was then removed. This solution was then added dropwise to the lithium phenoxide solution over a 5 minute period while maintaining the internal reaction temperature below 10 C. The mixture was aged at 0-10 C. for 2 hours, then 0.5M aqueous citric acid (150 mL) and MTBE (100 mL) were added. The organics were dried over MgSO4, filtered, concentrated in vacuo, and purified using silica gel chromatography (0:100 to 70:30 EtOAc:Hexanes) to provide compound 7 (8.1 g, 22.4 mmol, 92% yield). 1H-NMR delta (ppm)(DMSO-d6): 1.11 (6H, dd, J=6.3, 3.3 Hz), 1.20 (3H, d, J=7.1 Hz), 3.89-3.97 (1H, m), 4.79-4.84 (1H, m), 6.71 (1H, dd, J=14.2, 10.1 Hz), 7.24 (1H, t, J=7.4 Hz), 7.29 (2H, d, J=8.1 Hz), 7.42 (2H, t, 7.8 Hz), 7.86 (1H, d, J=2.0 Hz), 8.47 (1H, s), 8.53 (1H, d, J=2.1 Hz).

The synthetic route of 74115-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EDWARDS, John Simon; MULLENS, Peter Richard; CLEATOR, Edward; MAGUIRE, Courtney K.; SCOTT, Jeremy Peter; ZHONG, Yong; FREY, Lisa F.; DORMER, Peter G.; KLAPARS, Artis; ASHLEY, Eric; QIAN, Pu; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; Edwards, John; Mullens, Peter Richard; Cleator, Ed; Simmons, Bryon L.; Maguire, Courtney K.; Scott, Jeremy Peter; Yasuda, Nobuyoshi; Zhong, Yong-Li; Frey, Lisa F.; Dormer, Peter G.; Brunskill, Andrew; Klapars, Artis; Qian, Puneet; Zhang, Yi; Wan, Baoqiang; (23 pag.)US2017/275327; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 97483-77-7, 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. 97483-77-7, name is 5-Bromopicolinonitrile, molecular formula is C6H3BrN2, 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.

[0450] To a solution of5-bromopicolinonitrile (1.00 g, 5.46mmol) in DMF (10 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (2.77 g, 10.9 mmol),Pd(OAc)2 (61.0mg, 0.273 mmol), PPh3 (285 mg, 1.09 mmol)and KOAc (1.61 g, 16.4 mol) under a nitrogen atmosphere.The resulting mixture was stirred at 80 C. overnight. Thereaction mixture was cooled tort and the solids were removedby filtration. The filtrate was concentrated under reducedpressure to obtain a residue, which was purified by flashcolunm chromatography on silica gel with EtOAc/petroleumether (1 :50 v/v) to obtain compound 1f as a white solid (300mg, 24% yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C12H15BN20 2 : 231.1 (M+H). found: 231.1.

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 97483-77-7, 5-Bromopicolinonitrile.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6283-81-4 , The common heterocyclic compound, 6283-81-4, name is Ethyl 3-oxo-3-(pyridin-3-yl)propanoate, molecular formula is C10H11NO3, 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 12 To a mixture of ethyl nicotinoylacetate (2.30 g) and N,N’-dimethylurea (1.05 g) were added conc. hydrochloric acid (a few drops) and ethanol (1 ml) and the mixture was stirred at 110-115 C. for 4 hours under reduced pressure (30 mmHg). After being cooled to ambient temperature, the solution was adjusted to pH 7.0 with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated to give 6-(3-pyridyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (0.91 g). mp: 120-122 C. IR (Nujol): 1705, 1660 cm-1 NMR (DMSO-d6, delta): 8.68 (2H, m), 7.95 (1H, m), 7.53 (1H, dd, J=4.5 Hz), 5.70 (1H, s), 3.23 (3H, s), 3.10 (3H, s).

The synthetic route of 6283-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4612376; (1986); A;,
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. 77837-08-2, name is 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 77837-08-2

General procedure: Method 3: [0050] After 300 mg (1.39 mmol) of 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid was dissolved in 10 mL of acetonitrile, 415 mg (2.08 mmol) of 3-aminoquinuclidine dihydrochloride and 718 mg (5.56 mmol) of diethylisopropylamide were added to the solution. Afterward, 207 mg (1.53 mmol) of 1-hydroxylbenzotriazole (HOBt) and 266 mg (1.39 mmol) of N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDC) were added to the reaction solution. This reaction solution was stirred at room temperature for about 24 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo and then extracted three times with chloroform and an aqueous NaOH solution (pH=12), followed by purification using liquid chromatography (chloroform:methanol: ammonia water=10:1:0.1) to obtain a target compound (Actual yield: 317 mg, Percent yield: 70percent). [0051] 1H-NMR (CDCl3,200 MHz) delta8.11 (s, 1H), 7.75 (d, 1H), 7.40 (m, 4H), 6.65 (d, 1H), 6.26 (br, 1H), 4.15 (m, 1H), 3.39 (m, 1H), 2.89 (m, 4H), 2.53 (m, 1H), 2.06 (m, 1H), 1.53 (m, 4H)

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, 77837-08-2, 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid.

Reference:
Patent; SK BIOPHARMACEUTICALS CO., LTD.; Maeng, Cheol Young; Jang, Young Koo; Cha, Su Bong; Shin, Hye Won; Joung, Chan Mi; Cha, Hwa Ryun; Yi, Eun Jung; US2013/317059; (2013); 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. 13438-65-8, name is 2-Aminonicotinamide. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 122 1-(2,5-dichlorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-aminonicotinamide (0.2 g) in N,N-dimethylformamide (5 ml) was added 2,5-dichlorobenzylbromide (0.39 g) (Table 2, bromide 122), and the mixture was stirred at 80C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (0.21 g). 1H-NMR (DMSO-d6) d ppm 5.52 (2 H, s) 6.95 (1 H, d, J=2.27 Hz) 7.06 – 7.17 (1 H, m) 7.50 – 7.59 (1 H, m) 7.63 – 7.71 (1 H, m) 8.13 (1 H, s) 8.23 (1 H, d, J=5.30 Hz) 8.52 (1 H, d, J=6.82 Hz) 8.59 (1 H, s) 9.45 (2 H, s).

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, 13438-65-8, 2-Aminonicotinamide.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2077262; (2009); 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. 70201-43-3, name is 3-Bromoisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H4BrNO

Zn powder (10 g, excess) was added to a solution of 10 (4.8 g, 25.8 mmol) and allylbromide (3.9 mL, 50 mmol) in DMF under N2 at RT. The resulting mixture was stirred at RT for 1 hr, DMF was then removed in vacuo and the residue was partitioned into saturated aqueous Na2CO3 and ethyl acetate (150 mL). The aqueous layer was further extracted with ethyl acetate and the combined organic extraction was dried over Na2SO4. After concentration, the residue was purified by chromatography (SiO2, hexane/ethyl acetate, 5:1) to afford 11 (5.35 g, 91 %) as a light yellowish oil. 1H NMR (300 MHz, CDCl3), delta 8.58 (s, 1H), 8.44 (d, J = 5.4 Hz, 1H), 7.50 (d, J = 5.4 Hz, 1H), 5.76-5.92 (m, 1H), 5.12-5.22 (m, 2H), 4.98-5.04 (m, 1H), 2.82-3.00 (br, 1H), 2.60-2.68 (m, 1H), 2.25-2.34 (m, 1H). 13C NMR (75 MHz, CDCl3), delta 152.3, 151.9, 488.3, 132.8, 122.5, 120.1, 118.8, 70.5, 40.9. HRMS: m/e 226.9937, 228.9923 (Calcd for C9H10NOBr, 226.9942; C9H10NO81Br, 228.9919).

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, 70201-43-3, 3-Bromoisonicotinaldehyde.

Reference:
Article; Zhang, Zhenfa; Dwoskin, Linda P.; Crooks, Peter A.; Tetrahedron Letters; vol. 52; 21; (2011); p. 2667 – 2669;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1658-42-0, Methyl 2-(pyridin-2-yl)acetate, 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 Methyl 2-(pyridin-2-yl)acetate, blongs to pyridine-derivatives compound. Safety of Methyl 2-(pyridin-2-yl)acetate

General procedure: Ethyl 2-(pyridin-2-yl)acetate (1a, 0.4 mmol), 1,3-diphenylprop-2-yn-1-yl methyl carbonate (2a, 0.2 mmol),Pd2(dba)3 (0.01 mmol), DBFphos (0.02 mmol), K2CO3 (0.4 mmol)were mixed under N2 atmosphere in DMF (2 mL). The reactiontube was heated in an oil bath at 120 C for 16 h. After completionof the reaction, the reaction mixture was extracted withEtOAc (3 × 15 mL), and the solvent was removed under reducedpressure. The remaining crude product was then purifiedthrough column chromatography using silica gel (EtOAc-petroleumether = 1:5) to afford 3a as a white solid in 65% yield. 1HNMR (500 MHz, CDCl3): delta = 8.24 (dd, J = 9.2, 1.3 Hz, 1 H), 7.53 (d,J = 7.0 Hz, 1 H), 7.23-7.32 (m, 5 H), 7.15 (t, J = 7.3 Hz, 2 H), 7.10(t, J = 7.2 Hz, 1 H), 6.93- 6.99 (m, 3 H), 6.54 (td, J = 6.8, 1.3 Hz, 1H), 4.11 (q, J = 7.1 Hz, 2 H), 4.08 (s, 2 H), 1.06 (t, J = 7.1 Hz, 3 H).13C NMR (125 MHz, CDCl3): delta = 165.2, 137.5, 136.2, 135.4, 131.5,130.5, 128.9, 127.8, 127.7, 127.1, 126.7, 123.4, 122.2, 121.4,120.2, 112.6, 102.0, 59.3, 30.2, 14.3. HRMS (ESI): m/z [M + H]+calcd for C24H22NO2 : 356.1645; found 356.1642

The synthetic route of 1658-42-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Yuzhu; Wu, Ting; Fang, Youlai; Synlett; vol. 29; 14; (2018); p. 1909 – 1913;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem