Category: pyridine-derivatives

Reference of 1138444-17-3 ,Some common heterocyclic compound, 1138444-17-3, molecular formula is C5H2BrClIN, 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.

6-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to -78 C, followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at -78C for 1 h. 2- (benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0C and stirred for 2 h. The mixture was treated with saturated NH4C1 and extracted with ethylacetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54g, yield: 95%). MS (M+H): 344.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1138444-17-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); 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. 74936-72-4, name is 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylic acid (700g, 2.1mol) in methanol (14 L) was added Quinidine (617g, 1.90mol). The mixture was placed at 90C under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6 %.

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, 74936-72-4, 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-35-8 ,Some common heterocyclic compound, 13466-35-8, 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.

To a stirred solution of triphenylphosphine (814 mg, 3.10 mmol) in THF (7 ml) was added DIAD (603 mul, 3.10 mmol) at 0 oC. The mixture was stirred at 0 oC for about 10 min. To this mixture were added 3-chloro-2-hydroxypyridine (321 mg, 2.481 mmol) and tert- butyl 7-hydroxy-4-azaspiro[2.5]octane-4-carboxylate (470 mg, 2.068 mmol). The mixture was slowly warmed up to RT and stirred at RT overnight. The reaction was quenched with the addition of MeOH (~ 2 ml), and the mixture was concentrated and purified by Isco CombiFlash system on silica gel column (ISCO RediSep gold column, 80g) using 0-100%EtOAc/hexane to give the title compound as an oil after concentration. LCMS m/z [M+H]+ 283.13.

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. 13466-35-8, 3-Chloro-2-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane; FRADERA, Xavier; GUO, Liangqin; HAN, Yongxin; HE, Shuwen; HUANG, Xianhai; KOZLOWSKI, Joseph; LI, Guoqing; LIM, Jongwon; MARTINOT, Theodore, A.; PASTERNAK, Alexander; SCIAMMETTA, Nunzio; VERRAS, Andreas; XIAO, Li; YU, Wensheng; ZHANG, Rui; (146 pag.)WO2020/41100; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

To a solution of methyl 2,5-dichloroisonicotinate (2.25 g) in THF (50 mL) was added sodium borohydride (0.828 g), ethanol (20 mL) was added dropwise, and the mixture was stirred at 50C for 4 hr. To the reaction mixture was added 1 M aqueous hydrochloric acid solution. The solvent was evaporated under reduced pressure, and the obtained residue was diluted with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.90 g). MS (ESI+) : [M+H]+177.8.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-96-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1221171-96-5 as follows.

4-Amino-2-chloro-6-trifluoromethoxypyridine (45); At -78 0C, butyllithium (1.56 M in hexane, 2.2 mL, 3.4 mmol, 1.1 eq) was added dropwise to a solution of 2-chloro-4-iodo-6-trifluoromethoxypyridine (42, 1.0 g, 3.1 mmol) in THF (8 mL) followed after 10 min by benzenesulfonyl azide (0.6 g, 3.4 mmol, 1.1 eq). The reaction mixture was was allowed to reach 25 0C before being treated with a saturated aqueous solution of ammonium chloride (10 mL) and extracted with diethylehter (3 x 8 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford a crude red oil of 4-azido-2-chloro-6- trifluoromethoxypyridine. It was then dissolved in anhydrous diethylether (25 mL) and added dropwise to a suspension of lithium aluminium hydride (130 mg, 3.4 mmol, 1.1 eq) in diehtylether (25 mL). The reaction mixture was heated under reflux for 5 h before being treated with water (10 mL) and extracted with diethylether (3 x 10 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (1:9) as eluent which afforded pure 4-amino-2-chloro-6- trifluoromethoxypyridine (45, 0.3 g, 1.4 mmol, 46%) as a yellow oil.1H NMR (CDCl3, 300 MHz): delta = 6.41 (d, J = 1.6 Hz, 1 H), 6.07 (d, J = 1.6 Hz, 1 H),4.30 (bs, 2 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.8 – 13C NMR (CDCl3, 75 MHz): delta = 157.4, 156.7, 149.7, 119.9 (q, J = 260 Hz), 107.6, 96.0. – C6H4ClF3N2O (212): calcd. (%) C 33.90, H 1.90, N 13.18; found C 33.56, H 2.01, N 12.87.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-96-5, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); 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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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. Recommanded Product: 98121-41-6

EXAMPLE 2D 5-bromo-2,3-dichloropyridine A 5 L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1 H), 8.38 (d, J=3 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 98121-41-6.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242641; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, molecular weight is 206.2874, as common compound, the synthetic route is as follows.SDS of cas: 1018505-59-3

4-(2-Chloro-3-fluoro-pyrazinylamino)-2-pyrimidinecarboxylic acid (1.35 g, 1.2 eq),5-(4-Ethyl-piperazin-1-yl)-piperidin-2-amino (0.81 g, 1 eq) and triethylamine (500 muL)In DMF (15 mL) followed by HBTU (1.51 g, 1.5 eq).The mixture was stirred at room temperature for 16 hours.Then EtOAc (50 mL) and saturated NaHCO3 (15 mL)The layers were separated and the aqueous layer was extracted with EtOAc EtOAcThe combined organic layers were dried (MgSO4), filtered and evaporated.The residue was purified by column chromatography.1.42 g of the target compound 2 was obtained as a white solid(yield: 62%),Its nuclear magnetic resonance spectrum data is as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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-methoxy-4,6-dimethyl-nicotinonitrile (1.0 g, 6.166 mmol) was disolved in 30 mL of anhydrous methylene chloride and then added with 6 mL of trifluoro acetic acid and N-iodosuccinimide (2.2 g, 9.248 mmol) in this order while stirring at 0 C under the nitrogen atmosphere and then stirred again at room temperature for about 4 hours. The mixture was added with 60 mL of a saturated solution of sodium carbonate and 60 mL of a saturated solution of Na2S203 and then extracted twice with 80 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and filtered. A silica gel column chromatography (5% EtOAc/Hexanes) was performed on the resulting residue and 1.67 g (94%) of 5-iodo- 2-methoxy-4,6-dimethyl-nicotinonitrile was obtained in white solid. 1H NMR (300 MHz, CDC13) 5 2.64 (s, 3H), 2.75 (s, 3H), 4.01 (s, 3H).

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 41288-96-4, Adding some certain compound to certain chemical reactions, such as: 41288-96-4, name is 2-Chloro-5-hydroxypyridine,molecular formula is C5H4ClNO, 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 41288-96-4.

To a stirred solution of 6-chloropyridin-3-ol (3.0 g, 23.2 mmol) in N,N-dimethylformamide (30 mL) was added iodoethane (4.33 g, 27.8 mmol, 2.22 mL), and potassium carbonate (9.60 g, 69.6 mmol) at 0C. The reaction was warmed and stirred at 40 00 for 2 h. The reaction mixture was quenched by addition of water (30 mL) then the mixture was extracted with ethyl acetate (60 mL x 3). The combined organicphases were washed with saturated aqueous sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give 2-chloro-5-ethoxypyridine (3.30 g, 20.9 mmol, 90 %) as a yellow solid. 1H NMR (400 MHz, ODd3) O 7.97(d, J2.9 Hz, 1H), 7.17- 7.07(m, 2H), 3.99 (q, J7.0 Hz, 2H), 1 .36 (t, J7.0 Hz, 3H).

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. 41288-96-4, 2-Chloro-5-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63071-12-5, 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.63071-12-5, name is (6-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.

[0529] Synthesis of 2-(chlorometh -6-methoxypyridine: [0530] To a stirred solution of (6-methoxypyridin-2-yl)methanol (0.7 g 5.03 mmol) in CH2CI2 (20 mL) was added SOCl2 (2 mL) at 0 C under inert atmosphere. The resultant reaction mixture was heated up to 50 C and stirred for 2 h. After completion of starting material (by TLC), the volatiles were evaporated under reduced pressure. The residue was quenched with ice cold water and saturated NaHC03 and extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography to afford 2-(chloromethyl)-6-methoxypyridine (180 mg, 24%) as a liquid. 1H-NMR (DMSO d6, 500 MHz): delta 7.72 (t, 1H), 7.12 (d, 1H), 6.87 (d, 1H), 4.64 (s, 2H), 3.82 (s, 3H); LC-MS: 98.62%; 158.0 (M++l); (column; X- select C-18, (50×3.0 mm, 3.5mu); RT 4.12 min. 5mM NH4OAc in water: ACN; 0.50 ml/min); TLC: 10% EtOAc/Hexane (Rf: 0.6).

Statistics shows that 63071-12-5 is playing an increasingly important role. we look forward to future research findings about (6-Methoxypyridin-2-yl)methanol.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem