Day: April 18, 2022

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.73583-41-2, name is 4-Bromo-3-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.441, as common compound, the synthetic route is as follows.Application In Synthesis of 4-Bromo-3-chloropyridine

Step 1: Preparation of 3-chloro-4-((trimethylsilyl)ethynyl)pyridine A mixture of 4-bromo-3-chloropyridine (2 g, 10.5 mmol), bis(triphenylphosphine)palladium(II) chloride (0.37 g, 0.52 mmol), copper iodide (0.2 g, 1.05 mmol) in triethylamine (20 mL) was degassed and re-filled with nitrogen (2*). Then ethynyltrimethylsilane (4.4 mL, 31.4 mmol) was added dropwise by a syringe. After the addition, the reaction mixture was stirred at 60 C. for 18 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL*2). The combined organic phases were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (Biotage, 40 g silica, eluted with ethyl acetate in petroleum ether from 10% to 15%) to give 3-chloro-4-((trimethylsilyl)ethynyl)pyridine (1.47 g, 7.03 mmol, 67%) as a yellow oil. LCMS (ESI) m/z: 210.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73583-41-2, 4-Bromo-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); 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. 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 23056-47-5

To a solutionof 2-bromo-4-methyl-5-nitropyridine (5.00 g, 23.0 mmol) in tetrahydrofuran (THF)(30 ml) was added Raney nickel (slurry in water). The reaction mixture washydrogenated (balloon) overnight at room temperature. The mixture was filteredthrough Celite, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (0-50% EtOAc in hexanes) to afford27 as a yellow solid (4.02 g, 93%yield).1H NMR (300 MHz, CDCl3): delta ppm2.15 (d, J = 0.9 Hz, 3 H), 7.14 (s, 1 H), 7.78 (s, 1 H).

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, 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52334-51-7, 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. 52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one, molecular formula is C6H8N2O, 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.

[00266] Example 102: To a suspension of Example 12 (42 mg, 0.081 mmol) in sodium hydroxide (806 mu, 0.806 mmol) was added Example 102A (10 mg, 0.081 mmol). The reaction mixture was stirred at 40 C for over the weekend. The reaction was quenched with 1 N HC1 and MeOH. The organic layer was reduced in vacuo, and was purified using a 10 minutes gradient from 0 to 100%> B (Column: PHENOMENEX Axia Luna 100×20 mm 5u (10 min gradient). Solvent A: 10% ACN-90% H2O-0.1% TFA, Solvent B: 90% ACN-10% H2O-0.1% TFA) to give Example 102 (19 mg, 32% yield). lH NMR (400 MHz, MeOD) delta ppm 1.55 (s, 3H), 1.56 (s, 3H), 2.50 (s, 3 H), 3.25 – 3.27 (m, 1 H), 3.88 (d, J = 9.85 Hz, 1 H), 6.78 (d, J = 8.34 Hz, 1 H), 6.96 – 6.99 (m, 2 H), 7.09 – 7.13 (m, 1 H), 7.17 (d, J = 9.09 Hz, 2 H), 7.50 – 7.55 (m, 3 H), 7.93 (d, J = 8.08 Hz, 1 H), 7.98 (m, 1 H), 8.16 (m, 1 H). LCMS (ESI) m/z 590.0 (M+H)+, RT = 4.26 min (Method C).

According to the analysis of related databases, 52334-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120739-77-7, 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, molecular formula is C8H11ClN2, 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.

2): Synthesis of N-(6-chloropyridin-3-yl)methylene)-N-ethyl-1-(methylthio)-2-nitrovinylidene amine To a 100 ml three necked round bottom flask, N-(6-chloropyridin-3-yl-methylene)ethylamine (17.0 g, 0.1 mol), 1,1-bis(methylthio)-2-nitroethene (15.0 g, 0.09 mol), anhydrous ethanol (50 mL) were added. The mixture was refluxed until full convention and cooled to r.t., The reaction was concentrated with reduced pressure to obtain a crude product as dense liquid, which was purified by column chromatography to yield 5.3 g N-(6-chloropyridin-3-yl-methylene)-N-ethyl-1-(methylthio)-2-nitrovinylidene amine in 18.5% yield.

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 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine.

Reference:
Patent; EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY; US2010/298346; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1167056-96-3, Adding some certain compound to certain chemical reactions, such as: 1167056-96-3, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H4BrClN2, 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 1167056-96-3.

To a stirred solution of 3-bromo-5-chloro- 1H- pyrrolo[2,3-c]pyridine (AJ-2) (2.9 g, 12.6 mmol) in anhydrous DMF (100 mL) was added 2- chloro-6-(trifluoromethyl)benzoyl chloride (4.6 g, 18.9 mmol) and NaH (60%) (1 g, 25.2 mmol). The solution was stirred at r.t for 2 hours. The solution was quenched with H20 (400 mL). The suspension was extracted with EtOAc (150 mL x 3). The combined organic layer was washed with H20 (100 mL x 2) and brine (100 mL x 2) and dried over anhydrous Na2S04. The solution was evaporated and dried over vacuo and 5.7 g product was obtained. LCMS (ESI) calc’d for Ci5H6BrCl2F3N20 [M+H]+: 437, found: 437.

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. 1167056-96-3, 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26327; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 71670-70-7 , The common heterocyclic compound, 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride, 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.

The compound of Reference Example 48 (0.063g, 0.253mmol), 2- (chloromethyl) -5-methyl-pyridine monohydrochloride (0.050g, 0.281mmol), tetrabutylammonium chloride (0.008g, 0.0248 mmol), 50% aqueous potassium carbonate (0.280 g of) and tetrahydrofuran (3.0mL) the mixture was stirred overnight performed at 80 . After the reaction, diluted with water, and extracted with ethyl acetate. And the organic layers were combined, dried over sodium sulfate, filtered, concentrated, and the use of silica gel chromatography (chloroform: methanol = 9: 1) and the residue was purified to obtain the title compound (0.058g, 64%).

The synthetic route of 71670-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA CO., LTD.; YOSHINAGA, HIDEFUMI; URUNO, YOSHIHARU; SAWAMURA, KIYOTO; GOTO, NANA; IKUMA, YOHEI; (165 pag.)TW2016/5858; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77145-64-3, Adding some certain compound to certain chemical reactions, such as: 77145-64-3, name is 2-Chloro-6-(methylthio)pyridine,molecular formula is C6H6ClNS, 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 77145-64-3.

(Example 16) 2-chloro-6-methylthiopyridine (208 mg, 1.30 mmol) and N-chlorosuccinimide (17 mg, 0.13 mmol) were mixed with ethyl acetate (2 mL). 10% aqueous solution of sodium hypochlorite (2.2 g, 2.93 mmol) was added to the mixture at room temperature, and it was stirred for 1 hour. After that, ethyl acetate (10 mL) and sodium sulfite (164 mg, 1.30 mmol) were added to the mixture, and it was stirred. After stirring and separation, an organic layer was concentrated under reduced pressure, and the residue was subjected to purification by means of a silica gel column to obtain 2-chloro-6-methylsulfonylpyridine (244 mg, yield: 98 %).

According to the analysis of related databases, 77145-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2003116; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19346-43-1, 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.19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, molecular weight is 156.1145, as common compound, the synthetic route is as follows.

To 2-ethoxyethan-1 -amine (0.659 g, 7.40 mmol) in DMF (10 mL) were added 2-fluoro-4- methyl-3-nitropyridine (1 .05g, 6.73 mmol) and K2C03 (1 .022 g, 7.40 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was diluted with water (30 mL) and extracted with EtOAc (4 x 20 mL). The organic extracts were combined and washed with brine, dried over MgS04, filtered, and concentrated. Purification by chromatography on silica gel (0 to 30% EtOAc/hexanes) afforded N-(2-ethoxyethyl)-4- methyl-3-nitropyridin-2-amine (1 .52 g) as an orange color oil. LC-MS (ES) m/z = 226 [M+H]+. NMR (400 MHz, DMSO-c/6): 5 1 .1 1 (t, J =7.0 Hz, 3H), 2.39 (s, 3H), 3.46 (q, J = 6.8 Hz, 2H), 3.50 – 3.55 (m, 2H), 3.56 – 3.63 (m, 2H), 6.64 (d, J = 4.8 Hz, 1 H), 7.54 (t, J = 5.1 Hz, 1 H), 8.16 (d, J = 4.8 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 19346-43-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 582303-10-4 ,Some common heterocyclic compound, 582303-10-4, molecular formula is C8H11NO, 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 mixture of tri-n-butylphosphine (7.10 mL) , (2,6- dimethylpyridin-3-yl) methanol (3.00 g) , ethyl ( 6-hydroxy-l- benzothiophen-3-yl) acetate (5.43 g) and THF (150 mL) was added ADDP (7.17 g) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (7.74 g) XH NMR (300 MHz, CDC13) 61.19-1.32 (3H, m) , 2.54 (3H, s), 2.58 (3H, s), 3.81 (2H, d, J = 0.8 Hz), 4.17 (2H, q, J = 7.2 Hz), 5.08 (2H, s), 7.02 (1H, d, J = 7.9 Hz), 7.08 (1H, dd, J = 8.7, 2.3 Hz), 7.19 (1H, t, J = 0.9 Hz), 7.39 (1H, d, J = 2.3 Hz), 7.61 (1H, d, J = 7.6 Hz), 7.67 (1H, d, J = 8.7 Hz).

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. 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(Hydroxymethyl)-4-nitropyridine

To a stirred solution of (4-nitro-2-pyridyl)methanol (3530 mg; 22.3 mmol)[CAS 98197-88-7] in N,N- dimethylformamide (60 mL) were added imidazole (3070 mg; 44.7 mmol) and teri-butyl-chloro- dimethyl-silane (4080 mg; 26.8 mmol) at 0 C. The reaction mixture was allowed to warm up naturally to room temperature and stirred for 18 hours. The reaction mixture was quenched with distilled water (30 mL) and the product was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ether: ethyl acetate; 25: 1 ; v/v) to afford tert- butyl-dimethyl-[(4-nitro-2-pyridyl)methoxy]silane (5790 mg) as a light yellow oil. MS m/z (+ESI): 269.0 [M+H]+. ‘H-NMR (400 MHz, DMSO-O delta ppm: 8.89 (d, J= 5.2 Hz, 1H), 8.05 (d, J= 2.4 Hz, 1H), 8.01 (dd, Jl = 5.2 Hz, J2 = 2.4 Hz, 1H), 4.90 (s, 2H), 0.94 (s, 9H), 0.13 (s, 6H).

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, 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem