Category: pyridine-derivatives

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

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

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 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

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

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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-chloro-5-methylpyridine

A mixture of 66 (0.35g, 1.02mmol), 4-bromo-2-chloro-5-methylpyridine (0.32g, 1.53mmol) and K3PO4 (0.43g, 2.04mmol) in dioxane (15mL) was exchanged with argon twice, then PdPPh3)4 (0.11g, 0.1mmol) were added to the above mixture. The reaction mixture was heated to 100C and stirred for 4h under argon atmosphere. The mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 5%) to give the product as a white solid (0.3g, yield=69%). 1H NMR (400MHz, CDCl3) delta 8.25 (s, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 4.07 (d, J=7.0Hz, 2H), 3.99 (dd, J=11.3, 3.2Hz, 2H), 3.35 (td, J=11.8, 2.1Hz, 2H), 2.49 (s, 3H), 2.22-2.16 (m, 1H), 1.60 (s, 9H), 1.50-1.42 (m, 3H). LC/MS (ESI, m/z) 424.14 [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, 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1020253-14-8, 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 1020253-14-8 as follows.

This compound (14 mg, 0.026 mmol, 26% yield) as a white solid was prepared in a fashion similar to that described for Example 116, here using 116a (42 mg, 0.101 mmol) and 6-chloro-5-fluoronicotinonitrile (24 mg, 0.151 mmol) as starting materials. LC/MS (ESI+) m/z = 538.1 [M+H]+. NMR (400 MHz, CHLOROFORM-d) delta ppm 8.66 (d, J = 2.54 Hz, 1H) 7.97 – 8.02 (m, 1H) 7.70 (dd, J = 7.14, 2.64 Hz, 1H) 7.58 – 7.65 (m, 1H) 7.1 1 (dd, J = 1 1.54, 8.61Hz, lH) 6.62 (d, J = 14.87 Hz, lH) 6.42 (d, J = 14.87 Hz, 1H) 4.58 – 4.92 (m,2H) 3.54 – 3.75 (m, 8 H) 2.10 (t, J = 8.31Hz, 1H) 1.41 (dd, J = 9.59, 5.87 Hz, 1H) 1.08 (t, J = 6.36 Hz, 1H). N peak was not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1020253-14-8, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); 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. 58484-01-8, name is 3-Amino-2,6-dichloroisonicotinic acid, molecular formula is C6H4Cl2N2O2, 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. Product Details of 58484-01-8

Step 4 : Preparation of 6, 8-dichloro-2- [2- (3-chloro-pyridin -2-yl) -5-trifluoromethyl-2ff-pyrazol-3-yl] -pyrido [3, 4-d] [1, 3] oxazin-4-one; 5-Trifluoromethyl-2- (3-chloro-pyridin-2-yl) -2H-pyrazole-3- carboxylic acid chloride (example 2, step 3) (242 mg) was added to a mixture of 3-amino-2 , 6-dichloroisonicotinic acid (example 1, step 8) (190 mg) in acetonitrile (3 mL) . The mixture was stirred for 5 minutes at room temperature and triethylamine (220 muL) was added and stirred for 20 minutes, before a second portion of triethylamine (220 muL) was added. After the mixture was stirred for further 20 minutes at room temperature, methanesulfonyl chloride (70 muL) was added. After stirring for 2 hours at room temperature, the formed precipitate was filtered off, washed carefully with water and MTB-ether and dried in vacuum to afford 350 mg of the title compound of the formulaas a yellow solid. 1H-NMR (CDCl3, TMS) 6 (ppm) : 7.54-7.57 (2H, m) , 7.88 (IH, s), 8.01-8.04 (IH, m) , 8.56-8.58 (IH, m) .

With the rapid development of chemical substances, we look forward to future research findings about 58484-01-8.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 4684-94-0, 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.4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

6-Chloropyridine-2-carboxylic acid (1.20 g, 7.62 mmol) and ammonium chloride (0.81 g, 15.2 mmol) were dissolved in DMF (20 mL) and DIPEA (5.31 mL, 30.5 mmol), HONB (2.05 g, 11.4 mmol) and HBTU (4.33 g, 11.4 mmol) were added. The reaction mixture was stirred for 1 h and the solvents were removed in vacuo. The residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL) and the aq fraction was extracted with DCM (2*25 mL). The combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH/water to give the title compound (1.12 g, 94%) as a white solid. LCMS (ES+): 157.4 [MH]+.

Statistics shows that 4684-94-0 is playing an increasingly important role. we look forward to future research findings about 6-Chloropicolinic acid.

Reference:
Patent; Proximagen Limited; Savory, Edward Daniel; Stewart, Allson; Cartey, Allison; Brown, Giles; Simpson, Iain; Oliver, Kathryn; Patient, Lee; Higginbottom, Michael; Cole, Andrew Graham; US2013/289020; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53554-20-4 ,Some common heterocyclic compound, 53554-20-4, molecular formula is C6H4ClN3, 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.

38 (1.00g crude, max 4.30mmol), diethylzinc (1.0M in hexane, 7.81mmol, 7.8mL), and Pd2(PPh3)4 (150mg, 0.13mmol) were added to a microwave vial along with NMP (8mL). The vial was flushed with N2, sealed and heated using microwave irradiation at 100C for 30min. The contents of the vial were cooled to rt and washed with sat. aq. NaHCO3 (120mL), and H2O (120mL), dried over Na2SO4, and evaporated under vacuum. Purification by FC (heptane/EtOAc 80:20 to 50:50) afforded the product as brown solid (333mg, 53% over 2 steps). 1H NMR (CDCl3) delta 7.56 (d, J=8.5Hz, 1H), 6.34 (d, J=8.5Hz, 1H), 4.99 (b s, 2H), 2.86 (q, J=7.6Hz, 2H), 1.31 (t, J=7.6Hz, 3H). 13C NMR (CDCl3) delta 167.4, 159.8, 141.4, 118.5, 105.7, 96.6, 30.4, 13.5.

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem