Day: August 5, 2021

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

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

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

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

Electric Literature of 183208-35-7, 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

Under argon atmosphere, 1.86 g (9.4 mmol) of 5-bromo-7-azaindole was dissolved in 225 mL of dry acetonitrile and 45 mL of cc. acetic acid. The solution was heated to 40 C, 5 g of Selectfluor (l -Chloroniethyl-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafiuoroborate)) was added, and the resulting mixture was heated to 80 C’C, and stirred overnight. It was evaporated to dryness, and the crude product was dissolved in 200 mL of EtOAc, and washed twice with water. The organic layer was dried over NaiiSOr and was evaporated. After flash column chro atography (CHzCh/MeOH ::: 99/1) 362 mg of 5-bromo- 3-fluoro-7-azaindole was isolated.

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 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; RICHTER GEDEON NYRT.; LEDNECZKI, Istvan; ELES, Janos; TAPOLCSANYI, Pal; HORVATH, Anita; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; GALAMBOS, Janos; (0 pag.)WO2020/12424; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1149-23-1 , The common heterocyclic compound, 1149-23-1, name is Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate, molecular formula is C13H19NO4, 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: Equivalent amounts of 1,4-dihydropyridine (1, 3 mmol) and cupricbromide (3 mmol) were taken in a dry round-bottomed flask (25 mL) and ethylacetate-chloroform mixture (10 ml, v/v 1:1) was added to it. The flask wasfitted with a Liebig condenser fitted with a calcium chloride guard tube andwas refluxed for 1 h. The reaction was monitored by TLC after an interval of10 min. After completion, the reaction mixture was filtered through a flutedfilter paper, washed thoroughly with chloroform in order to remove theadhering cuprous bromide from the product and dried over anhydrous Na2SO4.Solvent was removed in vacuo and purified by column filtration to get pureproduct.

The synthetic route of 1149-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Saikh, Forid; De, Rimpa; Ghosh, Somnath; Tetrahedron Letters; vol. 55; 45; (2014); p. 6171 – 6174;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 136888-20-5 , The common heterocyclic compound, 136888-20-5, name is 5-Fluoro-3-nitropyridin-2(1H)-one, molecular formula is C5H3FN2O3, 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.

A mixture of the pyridine of preparation 55 (105 mg, 0.66 mmol), phosphorus oxychloride (1 ml) and Lambda/,Lambda/-dimethyIformamide (10 mul, catalytic) was heated at 11O0C for 18 hours. The cooled reaction mixture was then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane/acetonitrile as eluant (100:0 to 50:50 v/v) to yield the title compound (48 mg, 41%) as a solid. 1H NMR (400MHz, CDCI3): delta 8.03 (dd, 1 H), 8.55 (d, 1 H).

The synthetic route of 136888-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2006/114706; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-64-4, 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. 18368-64-4, name is 2-Chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

Fourth Step Production of methyl 3-(5-picoline-2-yl)aminosalicylate; Cesium carbonate (415 g), palladium acetate (8.8 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (25 g), methyl 3-amino-2-(2-methoxyethoxy)methyloxybenzoate (200 g) obtained in the preceding step, and 2-chloro-5-picoline (103 g) were added to toluene (1 L) in this order and stirred at 100° C. for 2 days. The reaction solution was filtered, and the filtrate was concentrated. Methanol (500 mL) and 6 N hydrochloric acid (200 mL) were added to the residue, and the mixture was refluxed and stirred for 0.5 hour. Active charcoal (25 g) was added to the reaction solution, and the mixture was stirred for 1 hour and then filtered. 1 N potassium citrate (2 L) was added to the filtrate, and the precipitated crystal was collected by filtration (218 g). The crystal collected by filtration was dissolved in ethyl acetate (1 L) and supplemented with silica gel (100 g), and the mixture was stirred at room temperature and then filtered. The filtrate was concentrated. The residue was recrystallized with acetone:water (2:1) (2 L), and the crystal was filtered and dried to obtain the title compound (128 g). (400 MHz, DMSO-d6): 2.18 (s, 3H), 3.92 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 7.35 (dd, J=7.9, 1.5 Hz, 1H), 7.42 (dd, J=8.4, 2.4 Hz, 1H), 7.98 (s, 1H), 8.19 (s, 1H), 8.48 (dd, J=8.2, 1.5 Hz, 1H), 11.30 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Japan Tobacco Inc.; US2007/149517; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53014-84-9 ,Some common heterocyclic compound, 53014-84-9, molecular formula is C7H7NO, 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.

A. Alpha-amino-alpha-(6-methyl-3-pyridinyl)acetonitrile To a solution of potassium cyanide (6.96 g, 107 mmol) and ammonium chloride (5.72 g, 107 mmol) in water (5 ml) was added 6-methyl-3-pyridin-carboxaldehyde (8.68 g, 71.5 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was basified with 50% NaOH and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to give the crude desired product in 7 g yield. The product was used without further purification.

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. 53014-84-9, 2-Methyl-5-formylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novo Nordisk A/S; US5328923; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128372-89-4 ,Some common heterocyclic compound, 128372-89-4, molecular formula is C10H15NO3, 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: A dried Schlenk flask was charged with arylboronic acid (3, 0.4 mmol), [Rh(L1)(OH)]2 (L1=(S,S)-Ph-thpe, 3.8 mg, 0.005 mmol), KHF2 (3.2 mg, 0.04 mmol), and 1 mL of anhydrous toluene under argon. The resulting mixture was stirred at room temperature for 30 min. 1-N-Boc-2-oxo-5,6-dihydropyridine (2c, 39.4 mg, 0.2 mmol) in toluene (1 mL) was added. Seven minutes later, 0.1 mL of isopropanol was added. After being stirred at room temperature for 2 h, the reaction was quenched with saturated aq NH4Cl, extracted with ethyl acetate (20 mL×3), and the combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel (300-400 mesh) column chromatography to afford 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128372-89-4, its application will become more common.

Reference:
Article; He, Zhi-Tao; Wei, Ya-Bing; Yu, Hong-Jie; Sun, Cai-Yun; Feng, Chen-Guo; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 68; 45; (2012); p. 9186 – 9191;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem