Day: April 18, 2022

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. 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloro-3-methylpyridine-2-carboxylic acid

To a solution of tert-butyl ((3aS,4R,8R)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39AB, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-chloro-3-methylpicolinic acid (92.8 mg, 0.53 mmol), followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by preparative TLC (silica gel, dichloromethane / ethyl acetate 1: 1, UV) to yield, after drying in vacuo, the title compound as a yellow solid (100 mg, 50% yield). MS (ES+) m/z 579.2 [M+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, 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-62-1, 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.

A solution of 2-([1,1?-biphenyl]-4-yl)-2,8-diazaspiro[4.5]decan-1-one 8 (TFA salt, 30 mg, 0.071 mmol) and 3-(trifluoromethyl)picolinaldehyde (18.74 mg, 0.107 mmol) in DCM (3 mL) and DMF (1 mL) was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (22.7 mg, 0.11 mmol) was then added. The reaction mixture was stirred at room temperature for overnight. The reaction was quenched with water (0.2 mL) and the reaction mixture was extracted with DCM (20 mL). The organic fraction was separated and dried over anhydrous sodium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by MDAP to afford compound 4h (13.5 mg, 33%) as a TFA salt. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.82 (d, J= 13.80 Hz, 2H), 2.17-2.29 (m, 4H), 3.27-3.45 (m, 2H), 3.51-3.59 (m, 2H), 3.90 (t, J= 6.53 Hz, 2H), 4.80 (s, 2H), 7.31-7.39 (m, 1H), 7.46 (t, J= 7.53 Hz, 2H), 7.63-7.77 (m, 5 H), 7.77-7.85 (m, 2H), 8.36 (d, J= 8.28 Hz, 1H), 9.00 (d, J= 4.27 Hz, 1H), 10.07 (br s, 1H). 13C NMR (100MHz, DMSO-d6) delta ppm 153.0, 139.8, 139.2, 136.3, 129.5, 127.8, 127.3, 126.8, 124.4, 120.3, 49.8, 45.0, 43.6, 29.4, 27.6. HRMS C27H27F3N3O (M+H)+ calcd 466.2106, found: 466.2112. LC/MS: tR= 2.94 min, 99.9%, m/z: 466.0 (M+H)+.

Statistics shows that 131747-62-1 is playing an increasingly important role. we look forward to future research findings about 3-(Trifluoromethyl)pyridine-2-carboxaldehyde.

Reference:
Article; Deng, Guanghui; Zhao, Baowei; Ma, Yingli; Xu, Qiongfeng; Wang, Hailong; Yang, Liuqing; Zhang, Qing; Guo, Taylor B.; Zhang, Wei; Jiao, Yang; Cai, Xin; Zhang, Jinqiang; Liu, Houfu; Guan, Xiaoming; Lu, Hongtao; Xiang, Jianing; Elliott, John D.; Lin, Xichen; Ren, Feng; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6349 – 6358;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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 solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO- , 5 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC MS (M+l)+ – 169.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; SHI, Zhi-Cai; CATO, Brian; KIM, Esther, Y.; WO2013/66718; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1370347-50-4, Adding some certain compound to certain chemical reactions, such as: 1370347-50-4, name is (S)-1-(3,5-Dichloropyridin-4-yl)ethanol,molecular formula is C7H7Cl2NO, 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 1370347-50-4.

(S) -1- (3,5-dichloropyridin-4-yl) ethanol (VI)(1.8 g, 9.37 mmol) and triethylamine (3.42 g, 50.61 mmol) were dissolved in anhydrous dichloromethane (50 ml) and methanesulfonyl chloride (1.29 g, 11.25 mmol) was added dropwise with stirring under ice bath. The reaction solution was poured into saturated sodium bicarbonate solution, the organic layer was separated, and the organic layer was washed with methylene chloride, and the organic layer was combined and the organic layer was washed with saturated brine. The organic layer was washed three times with the organic layer and the organic layer After drying over anhydrous sodium sulfate, the dichloromethane was distilled off under reduced pressure and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1) to give 2.15 g of pure white crystals in a yield of 93%

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. 1370347-50-4, (S)-1-(3,5-Dichloropyridin-4-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Wu, Yong; Hai, Li; Lei, Fan; Li, XiaoCen; (7 pag.)CN103819396; (2016); B;,
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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2369-19-9

(1) Synthesis of 2-fluoro-3-iodo-5-methylpyridine A 2.69 M n-butyllithium hexane solution (224 mL) was added dropwise to a mixture of diisopropylamine (92 mL) and THF (1.2 L) at -18C under a nitrogen atmosphere. Upon completion of the dropwise addition, the mixture was stirred while raising the temperature to -5C over a period of 20 minutes. The reaction mixture was cooled to -73C, and then a solution of 2-fluoro-5-methylpyridine (61 g) in THF (240 mL) was added dropwise thereto. The reaction mixture was stirred at -75C for 3.5 hours. A solution of iodine (139 g) in THF (24 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -75C for 1 hour and 55 minutes. Upon completion of the reaction, water (220 mL) was added to the reaction mixture at the same temperature. The mixture was stirred for 5 minutes at the same temperature. The reaction mixture was warmed to room temperature, and then water (1.2 L) was added. An aqueous sodium thiosulfate pentahydrate (136 g) solution (300 mL) and water (300 mL) were added to the mixture, and the resultant was stirred for 10 minutes. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layer was extracted with MTBE (1 L). The combined organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure. After adding n-heptane to the residue, the mixture was cooled. The precipitated solid was filtered out, and then was rinsed with n-heptane. The filtrate was cooled and the precipitated solid was filtered out. This procedure was repeated 5 times to obtain the title compound (109.69 g). 1H-NMR (400 MHz, CDCl3) delta (ppm):2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). ESI-MS m/z 238 [M+H]+

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; NORIMINE, Yoshihiko; SATO, Nobuaki; ISHIHARA, Yuki; TAKEDA, Kunitoshi; (65 pag.)EP2982674; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1053656-51-1, Ethyl 5-Boc-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-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, Computed Properties of C14H20N2O4S, blongs to pyridine-derivatives compound. Computed Properties of C14H20N2O4S

[00253] 1C. (Z)-Ethyl 5-( ,N’-bis(tert-butoxycarbonyl)carbamimidoyl)-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate: 5-tert-Butyl 2-ethyl 6,7- dihydrothiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate (0.500 g, 1.601 mmol) was treated with HC1 (4.0M in dioxane) (20.01 ml, 80 mmol) at room temperature. After 1 h, the precipitate was filtered, washed with Et20, and dried in vacuo. The amine hydrochloride salt was dissolved in DMF (10 mL) and treated with DIPEA (1.677 ml, 9.60 mmol) and (E)-tert-butyl (((tert-butoxycarbonyl)amino)( lH-pyrazol- 1 -yl)methylene)carbamate (0.497 g, 1.601 mmol). After 14 h, the reaction mixture was taken up in EtOAc (50 mL) and washed with water. The water layer was extracted with additional EtOAc. The combined organic layers were washed with 1.0M HQ solution, water, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography to give 1C (0.282 g, 38.8 % yield) as a white solid. MS (ESI) m/z: 455 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1053656-51-1, Ethyl 5-Boc-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; ORWAT, Michael J.; SMITH II, Leon M.; EWING, William R.; WO2014/59202; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153374-33-5, 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. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, 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.

General procedure: To a solution of 14a-d (2.5 mmol) in anhydrous dichloromethane (10 mL) anhydrous aluminum chloride (1.2 g, 8.8 mmol) was slowly added. The reaction mixture was stirred at room temperature (in the case of 15b) or heated under reflux for 10 min (in the case of 15a,c,d) and bromoacetyl bromide (0.2 mL, 2.5 mmol) in dichloromethane (2 mL) was added dropwise. The resulting solution was allowed to stir under reflux for 15-40 min. After cooling, water and ice were slowly added and the obtained precipitate was filtered off and purified by column chromatography using ethyl acetate (for compounds 15a, c) or dichloromethane/ethyl acetate (95/5) (for compound 15b,d) as eluent. For compounds 15b-d see supplementary material.

According to the analysis of related databases, 153374-33-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Carbone; Pennati; Barraja; Montalbano; Parrino; Spano; Lopergolo; Sbarra; Doldi; Zaffaroni; Cirrincione; Diana; Current Medicinal Chemistry; vol. 21; 14; (2014); p. 1654 – 1666;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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 500 mL round bottom flask containing 75 mL dry THF was dissolved 5- bromo-3-methyl-1 /-/-pyrazolo[3,4-c]pyridine (5.5 g, 25.9 mmol), and the contents were cooled to -15 0C. Sodium hydride (1.24 g (60% by wt., 31.1 mmol) was slowly added in portions to the cold stirring mixture, wherein vigorous gas evolution was observed (NOTE: Use caution during handling and addition of sodium hydride). After stirring for 15 min, benzenesulfonyl chloride (3.66 ml_, 28.5 mmol) was added dropwise via syringe. After stirring 15 min, the contents were removed from the cold bath and stirred with warming to room temperature over a 3 h period. The reaction mixture was poured onto a vigorously stirred solution of ice:water (1 :1 , 500 g), upon which the solid product crashes out. After stirring an additional 10 min, the heterogenous mixture was vacuum filtered and the filter cake was washed with additional water. The resultant solid was triturated with methanol (30 ml_), and the title compound is obtained as an off-white solid (10.75 g, 82%). 1H NMR: (CD3OD- d4) 9.27 (s, 1 H), 8.05 (s, 1 H), 8.01 (d, 2H), 7.69-7.73 (m, 1 H), 7.57-7.61 (m, 2H), 2.53 (s, 3H) ; LC/MS (MH+) = 351.8, 353.8; RT = 2.05 min.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-62-1 ,Some common heterocyclic compound, 131747-62-1, molecular formula is C7H4F3NO, 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 solution of 175 (100 mg, 0.776 mmol) in toluene 15 ml was added 66 (203.9 mg, 1.16 mmol). PTSA (452 mg, 2.303 mmol) was added to the reaction mass and stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 ml). The organic layer was dried over sodium sulphate and concentrated to get the crude 178, used in the next step without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-62-1, its application will become more common.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 851386-40-8, 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.851386-40-8, name is 4-Chloro-2,5-difluoropyridine, molecular formula is C5H2ClF2N, molecular weight is 149.53, as common compound, the synthetic route is as follows.

To a dry microwave vial under nitrogen was added (S)-isopropyl 2-(fert- butoxy)-2-(4-(4,4-dimethylpiperidin-l-yl)-2,6-dimemyl-5-(l,2,3,4-tetrahydroisoquinolin- 6-yl)pyridin-3-yl)acetate (46.8 mg, 0.090 mmol), 4-chloro-2,5-difluoropyridine (149.5 mg, 1.0 mmol), and acetonitrile (0.9 mL). The reaction was flushed briefly with nitrogen, treated with Hunig ‘s base (230 mu, 1.37 mmol), capped and heated in a microwave reactor at 85 – 95 C for 17h, followed by heating at 80 C for 36h in a sand bath. The crude reaction was purified via reverse phase Prep-HPLC to afford isopropyl (S)-2-(fert- butoxy)-2-(5-(2-(2,5-difluoropyridin-4-yl)-l,2,3,4-tetrahydroisoquinolin-6-yl)-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)acetate, 42 mg (quant). LCMS (M+l) = 635.4.

The chemical industry reduces the impact on the environment during synthesis 851386-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem