Category: pyridine-derivatives

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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-chloro-6-picoline

Example 633-[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-6-methyl-2-pyridinecarboxylic acidCla)2-Chloro-5-(2-chloro-6-methyl-3-pyridinyl)-JV-(tricyclo[3.3.1.13’7]dec-l-ylmethyl)-benzamideA mixture of [4-chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid (Example 2 (a)) (174 mg), 3-bromo-2-chloro-6-methyl-pyridine (104 mg),potassium carbonate (138 mg) and Z?w(triphenylphosphine)palladium(II) chloride (27 mg)in tetrahydrofuran (2 mL) and water (2 mL) was stirred at room temperature under anitrogen atmosphere over 72 hours. The mixture was filtered through diatomaceous earth,washing with methanol, and the filtrate was concentrated in vacuo. Purification bychromatography (SiOa, zsohexane:emyl acetate 1:1 as eluant) gave the sub-title compoundas a solid (135 mg).MS: APCI(+ve) 429/431 (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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1448427-99-3, Adding some certain compound to certain chemical reactions, such as: 1448427-99-3, name is 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine,molecular formula is C10H13N5, 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 1448427-99-3.

5-(4-Cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzoic acid hydrochloride (30 g,102 mmol) was suspended in anhydrous 1,2-dichioromethane (900 mL) at room temperature. Oxalyl chloride (18 ml, 205 mmol) was added while stirring under nitrogen, followed by N,N25 dimethylformamide (0.783 ml, 10.2 mmol). The mixture was stirred for about 4 hr at roomtemperature, and then the solvent was removed under reduced pressure. The residue was dissolved in about 600 mL anhydrous dichloromethane. 6-(4-Isopropyl-4H-1,2,4-triazol-3- yl)pyridin-2-amine (22.9 g, 113 mmol) and 4-dimethylaminopyridine (12.5g, 102 mmol) were rapidly added with stirring under nitrogen. The reaction was stirred for about 2 hours at roomtemperature and the dichioromethane was evaporated. The residue was dissolved in 500 mL water and solid NaHCO3 was added until the pH of the mixture was about 7. DichiOromethane was added (about 500 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 300 mL). The combined organics were washed with water (2 x 200 mL),dried over MgSO4, filtered and concentrated. The residue was dissolved in a minimum amount of THF, and water was added slowly until a thick slurry was formed. The solids were collected by filtration, washed with water, and dried.The solids obtained (about 72 g) were recrystallized from hot EtOH (Smug solid) and the solids collected by filtration, washed with 2:1 diethyl ether/EtOH, followed by diethyl ether and dried

According to the analysis of related databases, 1448427-99-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; ANDRES, Mark; CARRA, Ernest, A.; CHAN, Brenda, J. Burke; CHIU, Anna; LAPINA, Olga, Viktorovna; LATHROP, Stephen, P.; SMOLENSKAYA, Valeriya; YU, Lok, Him; (187 pag.)WO2016/105453; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, 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.

Example 1; Scheme A; A mixture of a-1 (0.0072 mol) and paraformaldehyde (0.0058 mol) in DMSO (3.5ml) and triton B (0.27ml) was stirred at 90C for 4 hours, then cooled to room temperature and purified by column chromatography over silica gel (eluent: CH2CI2 then CH2CI2/ CH3OH/NH4OH (99/1/0.1); 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.3 g of intermediate a-2 (20%).

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 18699-87-1, 2-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92276-38-5, Adding some certain compound to certain chemical reactions, such as: 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine,molecular formula is C5H3BrN4, 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 92276-38-5.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).[000224] Step 3: To a 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 0.127 mmol) was added trifluoroacetic acid (5 mL), and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by reverse-phase preparative HPLC using a mixture of water (containing 5% CH3CN and 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs diphenyl column as the stationary phase to afford 2-(4-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)phenyl)-N- (5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (12 mg, 22%) as a solid. ?H NMR (500 MHz, DMSO-d6) oe 11.41 (br s, 1H), 9.00 (d, J= 2.0 Hz, 1H), 8.60 (br s, 1H), 7.80 (d, J 8.5 Hz, 2H), 7.48 (d,J 8.5 Hz, 2H), 6.95 (s, 1H), 3.77 (s, 2H), 1.53 (s, 6H); LC-MS (ESI) m/z 431 (M+H).

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. 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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 ethyl 2-(4-bromopyridin-2-yl)acetate (1.72 g, 7.05 mmol) in THF (23.49 ml) was added dropwise LDA(4.05 ml, 8.10 mmol, 2M solution in THF) and the resulting mixture was stirred for 40 mm at-78C. Allyl bromide (0.610 ml, 7.05 mmol) was added dropwise, and the stirring was continuedat -78C for 2h and checked by LCMS (little desired product). The reaction mixture was slowly warmed to RT and stirred at RT for lhr (the reaction complete). The reaction was quenched by adding a saturated aqueous solution of NH4C1 (20 mL). The aqueous layer was extracted with Et20 (2 x 20 mL), the organic phases were combined, washed with HC1 (1 M, 20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash column chromatography on silica gel (1/1 EtOAc/Hex) to give the titlecompound. LC/MS = 285.77 [M+lj

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. 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 940943-37-3 , The common heterocyclic compound, 940943-37-3, name is S-(2-(6-(4-(3-(Dimethylamino)propoxy)phenylsulfonamido)pyridin-3-yl)-2-oxoethyl) ethanethioate, molecular formula is C20H25N3O5S2, 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.

[0202] Into 0.3088 g of Compound 1 was added 2 mL of methanol and 1.0 molar equivalent of hydrochloric acid (0.5 M in methanol, made from concentrated aqueous HCl solution) at approximately 60 0C. An additional 0.5 mL of methanol was added and the solution left to stir until only a small amount of solid remained. The sample was filtered through a 0.2 micron nylon filter. Seeds of HCl A were added and dissolved immediately upon addition. The solution was allowed to cool slowly to ambient temperature. Additional seeds (HCl A) were added and a light yellow precipitation followed. The solids were isolated by vacuum filtration and stored in a P205 desiccator (0.2373 g; yield 71%, based on unsolvated weight).

The synthetic route of 940943-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2808-86-8, 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.2808-86-8, name is 2,3,4,5-Tetrachloropyridine, molecular formula is C5HCl4N, molecular weight is 216.8801, as common compound, the synthetic route is as follows.

With a thermometer, reflux condenser,300 g of 2-chloropyridine was added to a 500 mL glass reaction vial of a chlorine tube.15g supported catalyst Sn-AC, heated to 110 C,Chlorine gas (pressure 0.1MPa) was introduced at a flow rate of 200 ml/min, and after 20 hours of reaction, the temperature was lowered to 30 C or lower.Filter to remove the supported catalyst,The obtained filtrate (HPLC detection of 2,3,4,5-tetrachloropyridine was 217 g) was placed in a glass reaction flask.And adding methanol-water mixed solvent 800mL (volume ratio 4:1),79 g of pyridine and 217 mg of activated carbon catalyst loaded with Pd (purchased from Xi’an Kaili New Materials Co., Ltd., grade 5% palladium carbon Pd/C, the same below), and the reaction system was repeatedly replaced with hydrogen three times.Then, it was heated to 50 C, and hydrogen gas (pressure 0.5 MPa) was introduced at a flow rate of 200 ml/min.At the same time, a 5% aqueous solution of Na2CO3 was added dropwise to maintain the pH of the reaction system at 8-10.HPLC analysis showed that the content of 2,3,4,5-tetrachloropyridine in the material was less than 5%, and the hydrogen was stopped.The material is lowered to normal temperature. The catalyst was filtered, and the filtrate was evaporated under reduced pressure to remove methanol, and the precipitated white solid was collected by filtration.The filter cake was washed three times with 100 mL of 5% hydrochloric acid and dried to give 465 g of white solid.HPLC analysis showed that the crude product contained 5.8% dichloropyridine and 89.8% 2,3,5-trichloropyridine.2,3,4,5-tetrachloropyridine 4.4%. The crude product was subjected to distillation under reduced pressure to obtain 414 g of 2,3,5-trichloropyridine (yield: 86.2%).The purity is greater than 99%.

Statistics shows that 2808-86-8 is playing an increasingly important role. we look forward to future research findings about 2,3,4,5-Tetrachloropyridine.

Reference:
Patent; Yancheng Heng Sheng Chemical Co., Ltd.; Huan Bin; Li Yong; Zhang Xiaohang; Cheng Ronghua; (9 pag.)CN108341767; (2018); A;,
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. 69422-72-6, name is 2,4,6-Trichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H2Cl3NO2

A solution of the product of EXAMPLE 11 C (1.5 g, 6.7 mmol) in dichloromethane (50 mL) was treated at room temperature with 2 drops of N, N-dimethylformamide. Oxalyl chloride (1.27 g, 10 mmol) was added dropwise over 15 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. Ammonium (gas) was passed through a solution of the acid chloride in tetrahydrofuran (20 mL) and the mixture stirred at room temperature for 0.5 hours. The mixture was concentrated under vacuum and the residue purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 225 (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, 69422-72-6, 2,4,6-Trichloronicotinic acid.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97683; (2012); 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 6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Nitro-2-oxo-3-pyridinecarboxylic Acid

Reference Example 11 Dimethylformamide (4 drops) was added to a solution of 2-hydroxy-5-nitronicotinic acid (5g) in phosphorus oxychloride (10ml). The mixture was stirred at the reflux temperature for 3 hours. Excess solvent was removed by evaporation and the residue was then poured carefully into water, keeping the temperature of the resulting mixture at below 40oC. The mixture was stirred at room temperature for a further 30 minutes then extracted with ethyl acetate. The extracts were washed with water, dried (magnesium sulphate) and evaporated. The resulting residue was triturated with ether/hexane to yield 2-chloro-5-nitronicotinic acid as a pale yellow solid (3.6g), m.p. 123-7oC.

With the rapid development of chemical substances, we look forward to future research findings about 6854-07-5.

Reference:
Patent; RHONE POULENC AGRICULTURE LTD.; EP634413; (1995); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52311-50-9, 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.52311-50-9, name is 2-Chloro-4-ethoxypyridine, molecular formula is C7H8ClNO, molecular weight is 157.6, as common compound, the synthetic route is as follows.

Step 2: 5-Bromo-2-chloro-4-ethoxypyridi 2-Chloro-4-ethoxypyridine (100 g, 634.5 mmol) was added to H2SO4 (500 mL) slowly. NBS (124.2 g, 698.0 mmol) was then added to the above reaction mixture at rt. The mixture was stirred at 80 C for 3 h. TLC analysis (PE/EA = 10: 1, Rf = 0.5) showed the reaction was finished. The reaction mixture was poured into ice-water (2000 mL), extracted with EA, and then concentrated. Another ten batches were prepared following the same procedure. The combined crude product was purified by flash column chromatography to give 5-bromo-2-chloro-4- ethoxypyridine (670 g, 2.84 mol, 40.0%): lH NMR (400 MHz, CD3OD): delta 8.31 (s, 1H), 7.14 (s, 1H), 4.32-4.10 (m, 2H), 1.58-1.35 (m, 3H); ES-LCMS m/z: 236.0, 238.0 (M, M+2H).

The chemical industry reduces the impact on the environment during synthesis 52311-50-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEMARTINO, Michael P.; GUAN, Huiping Amy; (103 pag.)WO2016/38552; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem