Category: pyridine-derivatives

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 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. 69045-84-7

Into a 500 mL autoclave, 51.2 g (0.2348 mol, 99%, 1.0 eq) of 2,3-dichloro-5-trifluoromethylpyridine and 160 mL of tetrahydrofuran were placed, and the autoclave was closed.Nitrogen was replaced three times at normal temperature, and 20.0 g (1.174 mol, 5.0 eq) of liquid ammonia was passed through the system, and the pressure in the system was about 0.6 MPa.The temperature was raised to 100 C to maintain the pressure reaction for 28 h.The system pressure was reduced from 1.6Mpa to 1.2Mpa, and the reaction of the raw material in the bottom tube sampling HPLC was complete. After the system is lowered to normal temperature, the pressure is released to normal pressure.The ammonia gas released is absorbed by tetrahydrofuran.The reaction solution was taken out, filtered, and rinsed with an appropriate amount of tetrahydrofuran, and the mother liquid was subjected to the next step of deamination.

Statistics shows that 69045-84-7 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-5-(trifluoromethyl)pyridine.

Reference:
Patent; Dalian Jiu Xin Fine Chemical Co., Ltd.; Inner Mongolia Jiaruimi Fine Chemical Co., Ltd.; Wang Rongliang; Wang Junchun; (10 pag.)CN110143916; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 98-98-6, name is Picolinic acid, 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 98-98-6. 98-98-6

Example 1Preparation of (R)-4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-(1-(hydroxyamino)-1-oxopropan-2-yl)picolinamide (Compound 1)Step 1a. Methyl 4-chloropicolinate (Compound 102); Anhydrous DMF (10 mL) was slowly added to SOCl2 (300 mL) at 40-48 C. The solution was stirred at room temperature for 10 minutes, and then compound 101 (100.0 g, 813.0 mmol) was added over 30 minutes. The resulting solution was heated at 72 C. (Vigorous SO2 evolution) for 16 h to generate a yellow solid. The resting mixture was cooled to room temperature, diluted with toluene (500 mL) and concentrated to 200 mL. The toluene addition/concentration process was repeated twice. The resulting solution and solid was added into 200 mL methanol at ice bath to keep the internal temperature below 55 C. The content were stirred at r.t. for 45 min, cooled to 5 C. and treated with Et2O (200 mL) dropwise. The resulting solid were filtered, washed with Et2O (200 mL) and dried under 35 C. to provide a white yellow solid. After the solid were solvated to hot water (500 mL, about 45 C.), NaHCO3 was added to adjust pH to 8-9. The mixture was extracted with ethyl acetate and the organic phase was concentrated to give desired compound 102 as a off-white solid (118.2 g, 85%). LCMS: 172 [M+1]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 98-98-6.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Gould, Stephen; Zhai, Haixiao; US2008/234332; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

4926-28-7, 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. 4926-28-7, name is 2-Bromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To 1.84 g ( 1 1.6 mmol) of KMn04 in 10 mL of H20 was added 0.65 mL (5.8 mmol) of 2-bromo-4-methylpyridine via syringe. The solution was refluxed for 1 hr, after which 1.25 equivalents ( 1.15 g; 7.25 mmol) of KMn04 was added. After an additional 2 hr reflux, 1.25 equivalents of KMn04 was added and stirred overnight to produce a dark solution containing a black suspension. After filtration through celite, the clear aqueous layer was washed with 3 x 20 mL of ethyl acetate. The aqueous layer was brought to a pH of 4 using 1M HC1 to precipitate out 237 mg of a white solid (yield = 20.3%). ESI-MS: m/z, 199.7 (calcd for M+ 199.9) NMR (DMSO-d6): delta 7.84 (dd, 1H, J = 5 Hz, l = lHz), 7.96 (s, 1H), 8.59 (d, 1H, J = 5 Hz), 14.02 (vbr, 1H).

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, 4926-28-7, 2-Bromo-4-methylpyridine.

Reference:
Patent; BERLINGUETTE, Curtis P.; KOIVISTO, Bryan; ROBSON, Kiyoshi; WO2011/32269; (2011); 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. 935-28-4, name is 2,6-Diethylpyridine. A new synthetic method of this compound is introduced below., 935-28-4

To the 25 mL Schlenk reaction tube was added 0.5 equivalents of NHPI and dried in vacuo for 15 minutes. The oxygen balloon was added and the acetonitrile lmL, 1.0 part by weight of tert-butyl nitrite, 0.5 mmol of 2,6-diethylpyridine were added in an oxygen atmosphere, In the reaction tube with poly tetrafluoro plug after the oil into the pot, 80 C reaction 24h After completion of the reaction, the solvent acetonitrile was concentrated under reduced pressure and the column eluted with petroleum ether / ethyl acetate (nu: 10: 1) to give 2-acetyl-6-ethylpyridine. Product yield 63%, light yellow oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound,935-28-4, 2,6-Diethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; University of Science and Technology of China; Kang Yanbiao; Liu Jie; (15 pag.)CN107011133; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

109-04-6, A common compound: 109-04-6, name is 2-Bromopyridine,molecular formula is C5H4BrN, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Method B: The preparation of 2-Bromopyridines with arylboronic acids was according to literature procedures.[1] To a 50-mL fire-dried flask was charged with 2-Bromopyridines (5 mmol, 1.0 eq), arylboronic acid (5.5 mmol, 1.5 eq), K2CO3 (1.38 g, 10.0 mmol, 2.0 eq), Pd(OAc)2 (56.0 mg, 0.25 mmol, 5.0 mol% ), PPh3 (131.0 mg, 0.5 mmol, 10.0 mol% ), CH3CN (10.0 mL) and methanol (5.0 mL). The mixture was degassed through a freeze-thaw-pump thread for three times. The reaction was stirred at 65 C for 24 hours. To the reaction mixture was added brine (15 mL) and ethyl acetate (15 mL). The phase was separated and the aqueous phase was extracted with ethyl acetate (4 ¡Á 15 mL). The combined organic phase was dried over Na2SO4 and concentrated under vacuum. The product was isolated by flash-column chromatography on silica gel (300-400 mesh).

With the rapid development of chemical substances, we look forward to future research findings about 109-04-6.

Reference:
Article; Zhong, Lei; Zong, Zhi-Hong; Wang, Xi-Cun; Tetrahedron; vol. 75; 17; (2019); p. 2547 – 2552;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

609-71-2, 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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (5). A stirred suspension of NaH 60% dispersion in mineral oil (206 mg, 5.14 mmol), washed twice with distilled n-hexane and once with Et20 under N2 atmosphere, was treated dropwise with a solution containing the 2-hydroxynicotinic acid (600 mg, 4.31 mmol) in 5 mL of anhydrous DMF. The mixture was left under stirring at rt for 2h and then 3,4-difluoro-benzylbromide (1 .06 g, 5.14 mmol) was added and the mixture stirred and heated at 50C for 1 6h. After, the mixture was concentrated under reduced pressure and the residue was treated with water to give a solid, which was collected by vacuum filtration. Next the solid was refluxed for 4h in aq. 10% NaOH (10 mL) and the resulting mixture was cooled and made acid with 1 N aq. HCI. The white solid formed was collected by filtration and washed with n-hexane and Et20, giving 5 as white solid (857 mg, 3.23 mmol, 75% yield). H-NMR (400 MHz, DMSO-de): delta 5.30 (s, 2H, CH2); 6.78 (t, 1 H, J = 6.9 Hz, Ar); 7.22-7.24 (m, 1 H, Ar); 7.41 -7.53 (m, 2H, Ar); 8.41 (d, 2H, J = 6.9 Hz, Ar) ppm. Anal. Calcd for C13H9NO3F2: C, 58.87%; H, 3.42%; N, (0126) 3%.

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. 609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (61 pag.)WO2017/211946; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

17368-12-6 , The common heterocyclic compound, 17368-12-6, name is 2-Chloro-4-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.

Method N. tert-Butyl 2-((2-acetylpyridin-4-yl)oxy)acetate To a solution of 2-chloropyridin-4-ol (500mg, 3.9mmol, l eq) in DMF (10ml) at 0C, was added NaH (60%, 188mg, 4.7mmol, 1.2 eq). After stirring 10 min at 0C, tert-butyl 2- bromoacetate (694ul, 4.7 mmol, 1.2 eq) was added, and the reaction was stirred an additional 20 minutes. The reaction was quenched with saturated aqueous ammonium chloride and partitioned in EtOAc/water. The organic was washed 2 x water, 1 x brine, dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography to yield tert-butyl 2-((2-chloropyridin-4-yl)oxy)acetate (793 mg, 83% yield) as a clear oil. 2-chloropyridin-4-ol (lOOmg, 0.41mmol, l eq), tributyl(l-ethoxyvinyl)stannane (166ul, 0.49mmol, 1 .2eq), PdCl2(PPh3)2 (14mg, 0.021mmol, 0.05 eq), in DMF (1 ml) was degassed under bubbling nitrogen and heated in a microwave reactor for 10 minutes at 140C. The reaction was partitioned in EtO Ac/water, extracted 3 x EtOAc, washed 3 x water, 1 x brine, dried over sodium sulfate and concentrated. The product was purified by silica gel chromatography to afford tert-butyl 2-((2-( l -methoxyvinyl)pyridin-4-yl)oxy)acetate (65 mg, 57% yield) as a light orange oil. tert-butyl 2-((2-(l-methoxyvinyl)pyridin-4-yl)oxy)acetate (230mg, 0.824 mmol, 1 eq) was dissolved in DCM (10ml). To this solution was added HCl/ether (2M, 2 ml). The reaction was stirred 3 hours at RT and concentrated under reduced pressure. rt-Butyl 2- ((2-acetylpyridin-4-yl)oxy)acetate (110 mg, 53% yield) was isolated as a white solid after purification by silica gel chromatography.

According to the analysis of related databases, 17368-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; AUGERI, David, J.; BENCIVENGA, Anthony, F.; BLANDEN, Adam; CARPIZO, Darren, R.; GILLERAN, John, A.; KIMBALL, Spencer David; LOH, Stewart, N.; YU, Xin; (70 pag.)WO2016/123253; (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. 55589-47-4, name is 3-Methylpicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. 55589-47-4

To a 50 mL RBF was added tert-butyl 4-(3-aminopropyl)piperazine-1-carboxylate (1.105 g, 4.54 mmol), DCE (Volume: 10.32 ml), 3-methylpicolinaldehyde (.5 g, 4.13 mmol) and STAB-H (1.575 g, 7.43 mmol). The reaction was stirred overnight then diluted with DCM and quenched with 2M NaOH. The organic layer was dried with Na2SO4, filtered and concentrated to a yellow oil which was purified via silica gel chromatography (DCM 2 minutes, 10percent B(80:20:3, DCM:MeOH:NH4OH) 5 minutes and 50percent B 9 minutes) to afford tert-butyl 4-(3-(((3-methylpyridin-2-yl)methyl)amino)propyl)piperazine-1-carboxylate (0.88 g, 2.53 mmol, 61 percent yield).1H NMR (400 MHz, CDCl3): delta = 8.37 (d, J= 5.0 Hz, 1H), 7.42 (d, J= 7.3 Hz, 1H), 7.07 (dd, J= 7.6, 4.8 Hz, 1H), 3.88 (s, 2H), 3.43 (t, J= 5.2 Hz, 4H), 2.79 (t, J= 6.8 Hz, 2H), 2.45 (t, J= 7.2 Hz, 2H), 2.39 (t, J= 5.2 Hz, 4H), 2.30 (s, 3H), 1.78 (pent, J= 7.0 Hz, 2H), 1.45 (s, 9H);

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55589-47-4, 3-Methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

89878-14-8, 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. 89878-14-8, name is 3-(Diethylboryl)pyridine, molecular formula is C9H14BN, 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.

To a well-stirred mixture consisting of 2-bromo-4-chloroaniline (5.0 g, 24 mmol) in tetrahydrofuran (180 ML), diethyl-3-pyridyl borane (4.07 g, 28 MMOL), and bis (TRIPHENYLPHOSOPHINE) PALLADIUM (II) chloride (2.53 g, 3.6 mmol), a solution of sodium carbonate (12.72 g, 120 MMOL) in water (60 ML) was added. The reaction was then heated at 75C for 18 hours. The layers of the biphasic mixture were separated, and the aqueous phase was extracted with an equal volume of ethyl acetate. The combined original reaction organic phase and ethyl acetate extract were dried and concentrated in vacuo to afford an oil (9.4 g). Flash chromatography of the entire sample (silica gel ; initial elution with ethyl acetate/hexanes = 8: 2 in volume followed by elution with pure hexane) afforded the title compound as a colorless oil (3.64 g, 74% yield). TLC Rf (silica gel plates ; elution with ethyl acetate, UV detection): 0.46.

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. 89878-14-8, 3-(Diethylboryl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/43929; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

16013-85-7, 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 16013-85-7 as follows.

Intermediate 6: 2,6-dibromo-3-nitropyridine (Scheme 12); A mixture of commercially available 2,6-dichloro-3-nitropyridine (10.0 g; 51.8 mmol) and 33 w% HBr/AcOH (120 mL) is heated at 80C for 3h. The solution is concentrated in vacuo, the resulting residue is taken into EtOAc and ished with saturated aqueous sodium bicarbonate. The organic phase is dried over sodium sulfate and concentrated in vacuo. The resulting product 14.4 g (99%) is used without further purification (Intermediate 6). GC/MS: 94% purity, tR 7.56 min (tR(SM) 6.93 min), m/z (CsI^B^) 280/282/284 (M, 38), 222/224/226 (35), 76 (100) Finnegan LCQ.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16013-85-7, its application will become more common.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/24666; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem