Pyridine-derivatives

Related Products of 153747-97-8, 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.

3.2.; 1-(5-bromo-2-pyridyl)piperazine 49 ml (272 mmol) of a solution of hydrochloric acid (6N) in isopropanol are added at room temperature to a solution of 18.60 g (54.40 mmol) of 1,1-dimethyl-ethyl 4-(5-bromo-2-pyridyl)-1-piperazinecarboxylate, obtained in step 3.1., in 100 ml of 1.4-dioxane. The reaction mixture is then maintained at about 60 C. for 3 hours. The mixture is concentrated to dryness under reduced pressure. The dihydrochloride obtained is taken up in 200 ml of dichloromethane and 200 ml of water, followed by portionwise addition, with stirring, of 10 g of sodium hydrogen carbonate. The phases are separated by settling, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. 12 g of product are obtained in the form of a white solid. m.p. ( C.): 72 C.

The chemical industry reduces the impact on the environment during synthesis 153747-97-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANOFI-AVENTIS; US2006/293310; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61494-55-1, Adding some certain compound to certain chemical reactions, such as: 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid,molecular formula is C7H6ClNO2, 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 61494-55-1.

2-chloro-3-pyridineacetic acid 50 g,Prepared into a 25% mass fraction of 2-chloro-3-pyridine sodium acetate solution,And 47 g of a 30% sodium hydroxide solutionSouring (the system may produce some insoluble polymer),Stir evenly after filtration,In the filtrate, 20% of Raney nickel catalyst was added,Heating up to 90-95 ,Through hydrogen reaction,In the atmospheric pressure or 1MPa pressure environment reaction,In the control,After the reaction is completed,After filtering the catalyst,The filtrate was adjusted to pH 4 with hydrochloric acid,Activated charcoal decolorization, desolate, offDry solvent (into a viscous fluid,And there is crystal presence (NaCl)Add 100 grams of anhydrous ethanol, fully dissolved,Filtration, the filtrate is 3-pyridine acetic acid in ethanol solution,The ethanol in the solution was removed (dried,Into a viscous fluid, can be added to the back of the amount of water,Dry the ethanol)Add water 50g, and add hydrochloric acid 35g,After sufficiently salt formation at 50 C,The solvent water is then dried (viscous solid)Cooling to room temperature,Plus 50g of absolute ethanol after washing,After filtration, the solid was rinsed with a portion of ethanol,Dry, that was finished3-pyridine acetic acid hydrochloride47.5 g, purity 99.1%, yield 95.0%.

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. 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Red Sun Biochemistry Co., Ltd.; Yue, Ruikuan; Chen, Honglong; Wang, Wenkui; Luo, Chaoran; Chen, Xinchun; Jiang, Jianhua; Ding, Yongshan; Zhong, Jinsong; Wang, Shugang; Zhan, Xinhua; (5 pag.)CN106366034; (2017); A;,
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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methyl-5-nitro-3-pyridinecarboxylic acid

A solution of1 (SO mg, 0.27 mmol), p-anisidine (51 mg, 0.41 mmol), PyBOP (281 mg, 0.54 mmol) and DIEA (0.14 ml, 0.81 mmol) in DCM/DMF (6 ml, 5:1) was stirred at 20C for 16 hr. The mixture was washed with sat. aq. NaHCO3, H2O, dried over MgSO4, evaporated and the brown residue was chromatographed on reverse phase HPLC (10-95% AcN in H2O) to give 12 (44 mg) as a pale brown solid. (Calculated mass: 328.3, observed mass: 328.5).

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, 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86521-05-3, 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 86521-05-3, name is 2-((Trimethylsilyl)ethynyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-trimethylsilylethynylpyridine (310 mg, 1.77 mmol) in THF (15 mL), a solution of NaOH (280 mg, 0.700 mmol, ca. 4 equiv) in MeOH (10 mL) was added, and the colorless reaction mixture was stirred for 5 min. The reaction mixture was diluted with Et2O (50 mL) and washed with water (50 mL) and brine (25 mL), dried with Na2SO4, filtered, and concentrated in vacuum. The resulting colorless oil was dissolved in Et3N (10 mL) and the solution flushed with argon while exposed to ultrasound for 10 min. This solution was transferred, via cannula to a solution of diiodo-TTF 8 (234 mg, 0.370 mmol) in argon-flushed Et3N (15mL) followed by addition of dppf (20.5 mg, 37.0 mumol, 10 mol%), Pd2dba3 (16.9 mg, 18.5 mumol, 5 mol%), and CuI (1.4 mg, 7.4 mumol, 2 mol%). The resulting cloudy orange to brown reaction mixture was exposed to ultrasound at 40 C for 30 min, after which the reaction mixture was heated by the means of conventional heating at 50 C for 30 min. According to TLC analysis (20% CH2Cl2/heptanes) no transformation had occurred. Pd(PPh3)4 (42.8 mg, 0.370 mmol) was added and the reaction mixture was flushed with argon for 10 min and then stirred for 2 h at 50 C. The resulting strongly wine-red reaction mixture was diluted with Et2O (100 mL) and washed with saturated aqueous NH4Cl (50 mL) and brine (50 mL), dried with Na2SO4, filtered, and concentrated in vacuum. Purification by flash column chromatography (CH2Cl2?15% EtOAc/CH2Cl2) gave 5b (168 mg, 0.288 mmol, 78%) as a red to black oil which solidified.

According to the analysis of related databases, 86521-05-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Broman, S°ren Lindbaek; Andersen, Cecilie Lindholm; Jevric, Martyn; Tortzen, Christian Gregers; Hammerich, Ole; Nielsen, Mogens Br°ndsted; Tetrahedron; vol. 72; 39; (2016); p. 5831 – 5842;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 477871-32-2, 6-Amino-5-bromonicotinonitrile, 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, Safety of 6-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. Safety of 6-Amino-5-bromonicotinonitrile

Step 2; 5-Bromo-6-chloro-nicotinonitrile; To a solution of anhydrous CuCl2 (77 mg, 0.58 mmol) in CH3CN (3 mL) add tert- BuONO (0.72 mmol). Heat the mixture at 65C and then add a suspension of the intermediate above (96 mg, 0.48 mmol) in CH3CN (2 mL). Stir the mixture for 3 hours. Cool at room temperature. Pour into HCI 3M and extract with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography on silica gel (eluent: hexane/EtOAc 2/1) to afford the title compound (55 mg, 55%). ‘H-NMR (DMSO, 300 MHz): 8.93 (s, 1H), 8.90 (s, 1H).

The synthetic route of 477871-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/90337; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256825-86-1, 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 1256825-86-1 as follows.

Bromine oxidation reaction:With 5 liters three bottles,Under mechanical agitation,60 g of 7-azaindole-6-carboxylic acid methyl ester,After adding 3.7 liters of tert-butanol,When the temperature was raised to 40 C,545 g of pyridine hydrobromide perbromide(PBPB) were added portionwise,At the end of 1 hour.And then kept at 40 C for 1 hour.Sampling monitoring,HPLC showed a starting material / product ratio of no more than 1%. Post-treatment and recrystallization:The reaction solution was poured into 5 liters of ice water, extracted with ethyl acetate (5 liters) at a temperature of 5 C, and the organic layer was collected.The mixture was concentrated to a volume of 1/3 solvent and poured into 3 liters of ice water. The solid was precipitated, filtered and the cake was washed with 500 ml of water and dried. Recrystallization was carried out using a 1: 5 weight ratio of ethyl acetate to methanol,Filtration,After drying under reduced pressure,Methyl 3,3-dibromo-2-oxo-7-azaindole-6-carboxylate (3), 85 g was obtained and sampled and HPLC showed a purity of 90%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256825-86-1, its application will become more common.

Reference:
Patent; SUZHOU HEJIAN MEDICAL TECHNOLOGY CO LTD; SHANG, XINJUN; LI, JIAHE; (8 pag.)CN104387385; (2016); B;,
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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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. HPLC of Formula: C6H6ClNO

A 50 mL solution of 7-[(5-methoxypyridin-2-yl)acetyl]-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane (2-1c, 1.30 g, 2.50 mmol) in de-oxygenated dioxane (nitrogen stream for 15 minutes) was prepared. A 2M solution of aqueous Na2CO3 solution (30 mL) was made and deoxygenated with a stream of nitrogen for 15 minutes. The above pinacolborate solution (2 mL, 0.1 mmol) was added to a plate of 24 vials containing the appropriate heterohalide; in this case 2-chloro-5-methoxypyridine (14.3 mg, 0.1 mmol). Pd(dppf)Cl2 catalyst (8 mg, 0.009 mmol) was added to each vial. The Na2CO3 solution (1 mL, 2M) was added to each vial using a multipipette. The reaction mixtures were sealed and heated to 110 C. while shaking for 5 hours. The dioxane was removed under vacuum. Ethyl acetate (2 mL) was added to each vial and, after shaking, the aqueous layer was discarded. The ethyl acetate solution was concentrated and the crude material purified directly by preparative HPLC eluting with water/acetonitrile. MS (ES) 499.13 (M+H)+. Retention time: 2.12 minutes XBridge C18 4.6×50 mm 5 um, 5-100% acetonitrile:water (0.1% formic acid).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; Bhattacharya, Samit K.; Cameron, Kimberly O.; Fernando, Dilinie P.; McClure, Kim F.; Kung, Daniel W.; Londregan, Allyn T.; Simila, Suvi T. M.; US2011/230461; (2011); 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 67625-36-9, name is Ethyl 5-chloroimidazo[1,2-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: Ethyl 5-chloroimidazo[1,2-a]pyridine-2-carboxylate

A mixture of the compound (1.28 g) obtained in (1), 4-chlorophenylboronic acid (1.78 g), tris(dibenzylidenacetone)dipalladium (0) chloroform adduct (0.34 g), 1,3-bis(2,6-diisopropylphenyl) imidazolium chloride (0.5 g), cesium carbonate (11.2 g) and dioxane (50 mL) was stirred for 24 hours at 80C. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue, which was then Celite filtered. Water was added to the filtrate, which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography and recrystallized from diisopropyl ether to obtain ethyl 5-(4-chlorophenyl)imidazo[1,2-a]pyridine-2-carboxylate (830 mg) as colorless crystals. 1H-NMR (CDCl3, 400MHz); delta 1.42 (3H, t, J=7.2Hz), 4.44 (2H, q, J=7.2Hz), 6.81 (1H, d, J=6.8Hz), 7.34 (1H, m), 7.56 (4H, m), 7.70 (1H, d, J=9.2Hz), 8.18 (1H, s)

With the rapid development of chemical substances, we look forward to future research findings about 67625-36-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1849465; (2007); 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. 10167-97-2, name is 2-Amino-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 10167-97-2

(a) 2-Amino-5-methoxypyridine (14.8 g, prepared by the method of J.G. Lombardino, J. Med. Chem. , 1981, 24 , 39) was dissolved in 60% hydrobromic acid (150 ml) and to the cooled (-10) stirred solution bromine (47.47 g) was added dropwise. To the resulting yellow suspension was added, dropwise, sodium nitrite (20.53 g) in water (40 ml), keeping the temperature below -5. The mixture was stirred to room temperature, and after 0.5 hour cooled to 0, and a solution of sodium hydroxide (120 g) in water (100 ml) was slowly added. The mixture was thoroughly extracted with ether, the combined ether extracts dried with anhydrous sodium sulphate, and evaporated. The residue was chromatographed on silica gel (150 g). Elution with dichloromethane gave a yellow oil (14.1 g, 63%) which was combined with a smaller batch (3.4 g) and distilled under reduced pressure to give 2-bromo-5-methoxypyridine (16.4 g). b.p. 76-78/0.6 torr.

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, 10167-97-2, 2-Amino-5-methoxypyridine.

Reference:
Patent; SMITH KLINE & FRENCH LABORATORIES, LIMITED; EP188351; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55404-31-4, 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 55404-31-4 as follows.

Example 1Synthesis of 3-bromo-4-methylpyridin-2(1H)-oneTo a resealable pressure vessel charged with 3-bromo-2-chloro-4-picoline (1.200 g, 5.81 mmol) was added formic acid (13.1 ml, 348 mmol) and H2O (4.00 ml,.222 mmol). The tube was sealed and the solution heated to 1200C. After 72 hrs, the solution was cooled to RT and concentrated in vacuo. The residue was purified by reverse phase chromatography (neutral) to afford 3-bromo-4-methylpyridin- 2(1H)-one as a white solid. MH+ = 188.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55404-31-4, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/8493; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem