Pyridine-derivatives

Reference of 1227594-89-9, 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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

[00640] tert-Butyl (1-((1r,4r)-4-hydroxycyclohexyl)-3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,2-c]pyridin-6-yl)(methyl)carbamate (0.037 g, 0.087 mmol),3-fluoro-4-(trifluoromethyl)pyridin-2-ol (0.0472 g, 0.261 mmol), PPh3 (0.0684 g, 0.261 mmol) were dissolved in THF (1 mL) and then DIAD (0.0527 g, 0.261 mmol) was added and the reaction was stirred overnight. The reaction mixture was concentrated and then dissolved in DCM (1 mL) and 4M HCl in dioxane (2 mL) was added and stirred for 2 h. The reaction mixture was concentrated and purified by C18 preparative HPLC (5-95% ACN in water with 0.2% TFA) to afford 1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-N-methyl-3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,2-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (12 mg, 19.3% yield). Mass spectrum (apci) m/z = 489.2 (M+H).1H NMR (CD3OD) delta 8.77 (s, 1H), 8.14 (d, 1H), 7.89 (s, 1H), 7.61 (s, 1H), 7.21 (m, 1H), 6.87 (s, 1H), 6.64 (s, 1H), 5.56 (s, 1H), 5.00 (m, 1H), 4.55 (m, 1H), 3.95 (s, 3H), 3.05 (s, 3H), 2.42-2.24 (m, 4H), 2.09-1.95 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); 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. 52605-96-6, name is 2-Chloro-3-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. Safety of 2-Chloro-3-methoxypyridine

The boronic acid was prepared as described in Intermediate 5 (2. 5 mmol ; crude) and was dissolved in acetonitrile (2ML) and added to A 5ML microwave vessel. To the solution was 3. 0 mmol OF 2-CHLORO-3-METHOXYPYRIDINE (432 MG), 29 mg of tetrakis (TRIPHENYLPHOSPHINE) palladium (0). After stirring until dissolution, 7. 5 mmol of potassium carbonate (1. 06 G) was added, followed by LML of water. The mixture was then heated at 160C for 300 seconds. After reaction completion, the solvents were evaporated under vacuum. The residue was dissolved in 2N KOH and THF and heated for 10 min. After hydrolysis, the THF was evaporated and the basic layer was washed with ETOAC. The aqueous layer was then acidified and extracted 3 times with EtOAc. The organic layers were combined and washed with water and brine. After drying, filtration and evaporation, the residue was TRITERATED with ether to give the desired product as A yellow solid (310MG ; 47%). MS : MH+= 260

With the rapid development of chemical substances, we look forward to future research findings about 52605-96-6.

Reference:
Patent; RENOVIS, INC.; WO2005/32493; (2005); A2;,
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. 183483-29-6, name is 2-(2-Bromopyridin-4-yl)acetic acid, the common compound, a new synthetic route is introduced below. Product Details of 183483-29-6

2-(2-Bromopyridin-4-yl)acetic acid (5 g, 23.1 mmol), benzene (40.5 ml) and MeOH (5.8 ml) were added to a 250 mL flask, thentrimethylsilyldiazomethane (11.6 ml, 23.1 mmol, 2 M) was added dropwise over 5 mm. The reaction was concentrated in vacuo. Silica gel chromatography using a hexanes/EtOAc gradient (0-100%) afforded the title compound.

The synthetic route of 183483-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88885; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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.

Under the protection of nitrogen,Add (0.188 mmol) to the reaction flask in turn.[Ir(COD)Cl] 2 (1,5-cyclooctadiene chloride dimer),R-(+)-1,1′-binaphthyl-2,2′-diphenylphosphine (0.188 mmol),150ml of dichloromethane,Stir at room temperature for 20 min,Then add potassium iodide 20.07g (0.0938mol)And 11.96 g (0.0938 mol) of 3-chloro-4-methylpyridine,The reaction flask was placed in a stainless steel autoclave and replaced with hydrogen three times.Finally, the required hydrogen pressure is 200 psi.After reacting for 12 hours at room temperature,Slowly release hydrogen,The reaction system was diluted with 150 mL of dichloromethane.Add 150 mL of saturated sodium carbonate solution, stir for 15 min, and separateOrganic layer,The aqueous layer was extracted with dichloromethane (3×150 mL).The organic layers were combined and dried over Na 2 SO 4 .The solvent was removed to give Compound III 16.84 g.The yield was 82.3%, and the HPLC purity was 99.55%.The ee value is 82%.

According to the analysis of related databases, 72093-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Shandong Yuxin Pharmaceutical Co., Ltd.; Song Lili; Meng Fanna; Liu Mingming; (8 pag.)CN108948021; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Add 2g of magnesium turnings, one iodine, a small amount of tetrahydrofuran (THF), and a small amount of 2-(2-bromophenyl)pyridine in a 500ml three-necked flask.After the reaction was initiated, 200 ml of a solution of 2-(2-bromophenyl)pyridine (19 g) in tetrahydrofuran (THF) was slowly added dropwise.After refluxing until the magnesium dust disappeared, 15 g of a solution of compound 3 in THF was added dropwise, 100 ml.The reflux reaction was continued for 8 hours, then the temperature was lowered to room temperature, and 2N hydrochloric acid was added to quench the reaction.The solvent was evaporated under reduced pressure, and 300 ml of acetic acid was added to the obtained solid, and the mixture was heated to reflux for 2 hours.The solvent was removed by filtration at room temperature.After the obtained white solid was dissolved in 100 THF, an equal amount of methanol was slowly added.The white solid product was precipitated to 16.3 g, and the yield was 72.6%.

Statistics shows that 109306-86-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromophenyl)pyridine.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Liu Kaipeng; Yang Yan; Yang Dandan; Zhang Hongke; Gao Renxiao; (25 pag.)CN108948030; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1033772-26-7, 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. 1033772-26-7, name is Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, molecular formula is C8H7N3O2, 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 solution of 1 H-pyrazolo[3,4-c]pyridine-5-carboxylic acid, methyl ester (1.5 g, 8.5 mmol) in THF (350 mL) at 0 0C was added LAH (958 mg) in two portions. The reaction was stirred at 0 0C for 1.5 hr, and at rt for 1 hr. The reaction was quenched with con. NaOH at 0 0C, and the solid was filtered off and washed with MeOH. The filtrate was concentrated. Purification by column afforded 1 H-pyrazolo[3,4-c]pyridine-5-methanol (1.23 g, 96%).

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 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/71451; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73672-37-4, 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. 73672-37-4, name is Ethyl 2-oxo-2-(pyridin-3-yl)acetate. A new synthetic method of this compound is introduced below.

Reference Example 36 A mixture of ethyl 3-pyridylglyoxylate (6.00 g), hydroxylamine hydrochloride (2.79 g), sodium acetate (4.13 g) and ethanol (80 ml) was heated to reflux for 15 hours. The reaction mixture was concentrated, water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain ethyl E-2-hydroxyimino-2-(3-pyridyl)-acetate (3.30 g, yield 51%) as colorless crystals. m.p. 172-173 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73672-37-4, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6251926; (2001); B1;,
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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (1.00 g, 4.35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (181 mg, 0.217 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), and potassium acetate (1.28 g, 13.0 mmol). Under nitrogen, anhydrous 1,4-dioxane (11 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 18 h. After cooling to rt, the reaction mixture was concentrated and the residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10) to afford 756 mg of crude aryl pinacolboranate intermediate (contaminated with pinacolborane by 1H NMR). Combining this intermediate (323 mg, ?1.17 mmol) with (+-)-(1S,2S)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (500 mg, 0.777 mmol), chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (32.8 mg, 0.0389 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (18.9 mg, 0.0389 mmol), and potassium phosphate tribasic monohydrate (554 mg, 2.33 mmol) in a vial, tetrahydrofuran (3.9 mL) and water (0.7 mL) were added under nitrogen and the vial was sealed and stirred at 80 C. for 19 h. The reaction mixture still contained starting material and so an equal aliquot of catalyst, ligand and water, as well as potassium phosphate tribasic monohydrate (184 mg, 0.777 mmol) and crude aryl pinacolboranate (215 mg, ?0.77 mmol) were added and stirred at 80 C. for 3 days. The mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10). The crude compound thus obtained was a yellow oil that contained the product according to HPLC-MS.

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, 886365-06-6, Methyl 5-bromo-4-methylpicolinate.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58602-02-1, 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. 58602-02-1, name is 2,6-Difluoro-3-nitropyridine, molecular formula is C5H2F2N2O2, 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.

b 2-(Ethylamino)-6-fluoro-3-nitropyridine To a solution of 2,6-difluoro-3-nitropyridine (45.7 g, 285 mmol) in THF (500 mL) at -40 C. was added drop-wise a solution of ethylamine (25.7 g, 570 mmol) in THF (250 mL). After 30 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane) to give the title compound (43.2 g, 82% yield) as a yellow solid.

According to the analysis of related databases, 58602-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Simoneau, Bruno; US2002/28807; (2002); 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. 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate

A clean, nitrogen purged reactor was charged with methylene chloride (471 L) and 2,3,3a,4,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (prepared according to Preparation Five, Step E, 47.0 kg, 1.0 eq.). The mixture was agitated and cooled to between -5C and 5C. The reaction mixture was slowly charged with triflouroacetic acid (117 kg, 7.5 eq.). The reaction mixture was warmed to a temperature between 20C and 30C and stirred for 12 to 15 hours. The reaction mixture was quenched by slow addition of an aqueous solution of 10% sodium carbonate (486 L, 0.5 eq.) at a temperature between 5C and 15C. The organic layer was separated and the aqueous layer extracted with methylene chloride (19 L). A mixture of acetone (456 L), water (56.4 L), and L-tartaric acid (22.6 kg, 1.1 eq.) was prepared in a second reactor. The tartaric acid mixture was combined with the organic layers at a temperature between 20C and 25C. The resulting slurry was heated to a temperature between 35C and 45C and stirred for 8 to 18 hours (overnight). When the reaction was judged to be complete, the slurry was cooled and granulated at a temperature between 0C and 10C for three to four hours and filtered. The product cake was washed with a mixture of acetone (40 L) and water (4.5 L). The product was dried under vacuum using only mild heat (applied if evaporation of acetone results in cooling). A yield of 37.7 kg of (3aR)-2,3a,4,5,6,7-hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one, (2R,3R)-2,3-dihydroxybutanedioate (1:1) was obtained (70.1% yield).

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, 193274-02-1, tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate.

Reference:
Patent; Pfizer Products Inc.; EP1031575; (2000); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem