Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, 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 C6H7Cl2N, blongs to pyridine-derivatives compound. Computed Properties of C6H7Cl2N

General procedure: Intermediate 9a (or 9b, 0.5 mmol) was dissolved in anhydrous DMF (10 mL) in the presenceof anhydrous K2CO3 (0.14 g, 1 mmol), followed by addition of appropriate substituted benzyl chloride (or 4-picolyl chloride hydrochloride) (0.5 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water (20 mL) was added. Extracted with ethyl acetate (2 × 10 mL), and the organic phase was washed with saturated sodium chloride solution (10 mL), and dried over anhydrous Na2SO4, which was purified by flash column chromatography to afford title compounds 10a1~a3 and 10b1~b3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Chen, Xuwang; Liu, Xin; Meng, Qing; Wang, Ding; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Balzarini, Jan; Liu, Xinyong; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6593 – 6597;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 93683-65-9, 6-Chloro-3-nitropicolinonitrile, 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, 93683-65-9, blongs to pyridine-derivatives compound. Product Details of 93683-65-9

To a 1 L flask was added 2 (20.0 g, 108.8 mmol), 400 mL CH2Cl2,TBAB (16 g, 52 mmol) and a solution of rongalite (140.4 g /400 mL H2O) in proper order, the suspension wasstirred acutely at room temperature for 2 hours, after addition of another 75.2 g rongalite, the reaction mixturewas kept stirred for another 1.5 hours. After the reaction, the mixture was neutralized with saturated potassiumcarbonate and stirred for 30 minutes, then the mixture was poured into separator funnel and separated to obtainthe organic phase, the aqueous phase was extracted with CH2Cl2 (300 mL ×2), the organic phase was collectedand dried with MgSO4. After concentrating to saturate state, it was salified with hydrogen chloride saturated indiethyl ether. The white solid appeared was filtered, dissolved in water and precipitated absolutely with additionof aqueous ammonia. The mixture was filtered again to yield 14.6 g white solid (40%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,93683-65-9, its application will become more common.

Reference:
Article; Fan, Yin-Bo; Li, Kun; Huang, Min; Cao, Yu; Li, Ying; Jin, Shu-Yu; Liu, Wen-Bing; Wen, Jia-Chen; Liu, Dan; Zhao, Lin-Xiang; Bioorganic and Medicinal Chemistry Letters; vol. 26; 4; (2016); p. 1224 – 1228;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884495-39-0, 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 884495-39-0 as follows.

5-Bromo-2-methoxypyridin-3-amine (1 .73 g, 6.82 mmol) was dissolved in 50 mL dioxane. Bis(pinacolato)diboron (4.4 g, 17.33 mmol) and potassium acetate (2.5 g, 25.47 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Then bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.9 g, 0.16 mmol) was added under argon conditions and the mixture heated at 80C for 2h. The reaction mixture was partitioned between ethyl acetate and water and filtered through a plug of celite. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1Purification System (0% to 20%, hexane-ethyl acetate) to obtain 1 .43g. This solid was triturated with hexane, filtered and dried in the vacuum oven to give 0.94 g (55% yield) of the desired product as a solid. Purity 100%.LRMS (m/z): 251 (M+1 )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-39-0, its application will become more common.

Reference:
Patent; ALMIRALL, S.A.; ERRA SOLA, Montserrat; CARRASCAL RIERA, Marta; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; BERNAL ANCHUELA, Francisco Javier; PAGES SANTACANA, Lluis Miquel; MIR CEPEDA, Marta; CASALS COLL, Gaspar; HERNANDEZ OLASAGARRE, Maria Begona; WO2014/60432; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 39856-50-3 ,Some common heterocyclic compound, 39856-50-3, molecular formula is C5H3BrN2O2, 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.

Under a nitrogen purge, the solid 4-bromo-2-nitropyridine (10. Ig; 0.05mol), potassium carbonate (10.5g; 0.075mol; -325mesh), tetrabutylammonium iodide (1.25g; 5mol%), and piperazine (5.4g; 0.0625mol) were sequentially added to 80ml acetonitrile. The suspension was heated to reflux, and maintained for 16 h. The now-bright yellow suspension was filtered hot, and the filter cake washed with a few portions of hot acetonitrile, such that the filtrate flows only slightly yellow. The filtrate quickly deposited a yellow/orange solid. This was reheated to obtain a clear solution, which was placed in the refrigerator for 16 h. The yellow/orange solid was isolated by filtration and the filter cake was washed with small portion cold CH3CN, followed by a small portion of petroleum ether. Air drying the solid provided ca 10.2g of solid material, about 65% of theory. Another 2g of material was isolated by evaporating the acetonitrile filtrate down to a semi-solid and then recrystallizing the residue from a minimum amount of hot isopropanol (treated with activated charcoal). NMR: 1.63 (s, IH), 2.99 (m, 4H), 3.36 (m, 4H), 7.14 (m, IH), 8.08 (m, 2H), m/z 209.

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. 39856-50-3, 5-Bromo-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/95159; (2006); 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.58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 2-chloroisonicotinate

To a suspension of lithium aluminum hydride (221 mg) in Et2O (10.0 mL) cooled to -40C was added methyl 2-chloroisonicotinate (1.00 g) in Et2O (2 mL) dropwise and the mixture was stirred at -4 0C for 30 min and quenched with water. The aqueous layer was extracted with EtOAc three times. The combined organic layer was washed with aqueous saturated NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure to give (2-chloropyridin-4-yl)methanol (641 mg) as a pale brown solid.1HNMR (300 MHz, CDCl3, delta): 2.81-2.93 (m, IH), 4.72-4.80 (m, 2H), 7.17-7.26 (m, IH), 7.34-7.41 (m, IH), 8.30 (dd, J= 5.1, 0.6 Hz5 IH); ESI MS m/z 144 (M++., 100percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-11-1, Methyl 2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); A1;,
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. 65515-28-8, name is Methyl 2,6-dichloronicotinate, the common compound, a new synthetic route is introduced below. Product Details of 65515-28-8

A solution of 4-chlorophenol (12.2 g, 0.095 mol) in 36.6 mL of DMF was added at room temperature to the above solution (19.6 g of ester 2, 0.095 mol), followed by addition of triethylamine (17.3 mL, 0.124 mol) at 20-22 0C over 15 min. Solid DABCO (1.6 g, 14.2 mmol) was added to the resulting solution in one portion. A temperature increase of ~3 0C was observed. A water bath was used to maintain the reaction temperature. The reaction was stirred at 22-24 0C for 4-5 h while monitoring by LC until all of the 4- chlorophenol was consumed, resulting in a light slurry. AcOH (2.72 mL, 47.5 mmol) and IPA (57.5 mL) were added to the light slurry, followed by cold water (30 mL) to maintain the internal temperature at 20-25 0C. When the water was added, a clear solution first formed, and then a slurry of product formed. After stirring at RT for 0.5 h, additional water (86 mL) was added over 0.5 h. After the slurry was stirred at RT for 1-2 h, it was filtered. The filter cake was washed with mixed solvents (60 mL OfIPAiH2O = 1:1). The isolated solid was dried in a vacuum-oven at 50 0C for 8 h to provide the product as white cotton-like solid.

The synthetic route of 65515-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/96564; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7356-60-7, 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. 7356-60-7, name is Nicotinimidamide hydrochloride, molecular formula is C6H8ClN3, 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.

Step 3: To a solution of nicotinamidine hydrochloride (1 g, 6.35 mmol) in anhydrous DMF (12 mL) is added sodium salt of 2-dimethoxymethyl-3-hydroxy-acrylicacid methyl ester (1.46 g, 7.36 mmol) and the reaction mixture is heated at 1000C under N2 for 3 hours. After this time the reaction is cooled to room temperature and water (48 mL) is added. The precipitate is collected by filtration, washed with water and vacuum dried to afford 2-pyridin-3-yl- pyrimidine-5-carboxylic acid methyl ester (0.7 g, 51%). MS: 216 (M+H).

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 7356-60-7, Nicotinimidamide hydrochloride.

Reference:
Patent; SANOFI-AVENTIS; WO2008/121670; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 633328-33-3, name is 3-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Example i-2: Preparation of 3-bromo-1H-pyrazolo[4,3-b]pyridine Step 1. Preparation of (3-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)(2-chloro-6- (trifluoromethyl)phenyl)methanone (i-2). To a flask was added 3-bromo-lH-pyrazolo[4,3-b]pyridine (i-2a) (3.2 g, 16.2 mmol), 2- chloro-6-(trifluoromethyl)benzoyl chloride 2 (3.9 g, 16.2 mmol), DMAP (1.97 g, 16.2 mmol) and DCM (60 mL), followed by the addition of TEA (3.26 g, 32.4 mmol) slowly. The reaction mixture was stirred at 40C for 3h. The mixture was diluted with H20, and the organic layer was separated. The aqueous layer was extracted with CH2C12 . The combined organics were washed with H20, brine, dried over Na2S04, and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc, 5/1) to afford 3.0 g (46%) of the title compound. LCMS (ESI) calc’d for Ci4H6BrClF3N30 [M+H]+: 406, found: 406.

With the rapid development of chemical substances, we look forward to future research findings about 633328-33-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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.39856-50-3, name is 5-Bromo-2-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of compound (1) (20.00 g, 98.53 mmol, 1.00 eq) in dimethyl sulfoxide (52 mL), compound (2) (24.00 g, 128.86 mmol, 1.31 eq) and triethylamine (20.00 g, 197.65 mmol, 2.01 eq) were added. The solution was heated to 60 C. and stirred for 18 hours. TLC (petroleum ether:ethyl acetate=3:1) showed the completion of the reaction. The solution was diluted with water (200 mL), stirred for 30 minutes, and then filtered. The filter cake was washed with water and dried under vacuum to obtain a crude product. The crude product was purified by a silica gel column (petroleum ether:ethyl acetate=50:1 to 20:1) to obtain compound (3) (27.00 g, 87.57 mmol, yield: 88.87%). 1H NMR (400 MHz, CDCl3) delta8.18 (d, J=9.03 Hz, 1H), 8.13 (d, J=2.89 Hz, 1H), 7.21 (dd, J=9.10, 2.95 Hz, 1H), 3.69-3.59 (m, 4H), 3.51-3.40 (m, 4H), 1.49 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 39856-50-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55717-45-8, 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.55717-45-8, name is 6-Bromopyridin-3-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

Compound (II-3) (5.00 g, 28.7 mmol) was dissolved in DMF (30 mL), potassium carbonate (7.94 g, 57.5 mmol),benzyl bromide (4.1 mL, 35 mmol) and TBAI (531 mg, 1.44 mmol) were added under ice-cooling, and the mixture waswarmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydroussodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (n-hexane:ethyl acetate = 97:3 ?80:20) to give compound (M-16) (yield 6.97 g, 92%) as awhite solid

Statistics shows that 55717-45-8 is playing an increasingly important role. we look forward to future research findings about 6-Bromopyridin-3-ol.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem