Pyridine-derivatives

Reference of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, 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.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

According to the analysis of related databases, 83766-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 947249-13-0, 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. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, 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 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 13.39 mmol) in 1,4-dioxane (60 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (3.74 g, 14.73 mmol), tricyclohexylphosphine (525 mg, 1.87 mmol), potassium acetate (3.28 g, 33.47 mmol) and tris(dibenzylideneacetone)dipalladium(0) (490 mg, 0.53 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C. for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3*75 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25% ethyl acetate in hexane) affording 3-(difluoromethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.3 g, 34%): 1H NMR (400 MHz, DMSO-d6) delta 8.03 (s, 1H), 7.33 (s, 1H), 7.11 (t, J=73.6 Hz, 1H), 6.44 (s, 2H), 1.25 (s, 12H).

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 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; GENENTECH, INC.; Siu, Michael; Estrada, Anthony; Liu, Wen; Lyssikatos, Joseph P.; Patel, Snahel; Liang, Guibai; Chen, Kevin; US2015/175619; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-99-1, 4-Bromo-2-methylpyridine, 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, 22282-99-1, blongs to pyridine-derivatives compound. Product Details of 22282-99-1

[0566] Step 1: ethyl 2-(4-bromopyridin-2-yl)acetate – To a stirred solution of 4-bromo-2-methylpyridine (1.2 g, 4.93 mmol, 1.0 eq) in THF (15 mL), was added diethyl carbonate (0.698 mL, 5.92 mmol, 1.2 eq) and the mixture stirred at -78C under nitrogen atmosphere. LDA(2′-78C for 2h. The reaction was then quenched with saturated sodium chloride solution and the product extracted with EtOAc (2′-(4-bromopyridin-2-yl)acetate (0.500 g, 30%) as a pale yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-99-1, its application will become more common.

Reference:
Patent; CAPULUS THERAPEUTICS, LLC; GREEN, Michael John; HART, Barry Patrick; (341 pag.)WO2019/148125; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1014631-89-0, 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 1014631-89-0, name is 1-(Pyridin-3-yl)-1H-pyrazole-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Stage 3: N-(Dimethylsulphamoyl)-1-(pyridin-3-yl)-1H-pyrazole-4-carboxamide 0.250 g (1.32 mmol) of 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylic acid was initially charged in 5 ml of tetrahydrofuran, and 0.43 ml (1.98 mmol) of N,N’-carbonyldiimidazole was added. The mixture was heated under reflux for 1 h. 0.246 g (1.98 mmol) of N,N-dimethylsulphonamide was dissolved in 3 ml of tetrahydrofuran and added dropwise at room temperature to the first solution. The mixture was stirred at room temperature for 10 min. After addition of 0.30 ml (1.98 mmol) of 1,8-diazabicyclo(5.4.0)undec-7-ene, the mixture was stirred at room temperature for 12 h. The solvent was removed on a rotary evaporator and water was added to the residue. The aqueous phase was extracted with dichloromethane. The organic phase was discarded and the aqueous phase was acidified with concentrated HCl. The precipitate formed was filtered off with suction. Yield: 0.120 g (30% of theory), logP1) (HCOOH) 1.03 1H NMR ((CD3)2SO): 2.89 (s, 6H), 7.58-7.62 (m, 1H), 8.24-8.27 (m, 1H), 8.38 (s, 1H), 8.60-8.62 (m, 1H), 9.10-9.11 (m, 1H), 9.22 (s, 1H) ppm.

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 1014631-89-0, 1-(Pyridin-3-yl)-1H-pyrazole-4-carboxylic acid.

Reference:
Patent; Bayer CropScience AG; US2012/95023; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89570-84-3, 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. 89570-84-3, name is 2-Hydrazinyl-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

631 mg (3.0 mmol) of the compound from Example 3A and 531 mg (3.0 mmol) of the compound from Example 25A are initially introduced into 10 ml ethanol. 114 mg (0.6 mmol) p-toluenesulfonic acid monohydrate are added and the mixture is stirred under reflux for 16 h. It is then concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product fractions are combined, the solvent is removed and the residue is dried under a high vacuum. 20 ml of a 4 N solution of hydrogen chloride in dioxane are added and the mixture is stirred at RT for 1 h. The solid is filtered off, washed twice with tert-butyl methyl ether and dried under a high vacuum.Yield: 231 mg (23% of th.)LC-MS (Method 8): Rt=1.65 min; MS (ESIpos): m/z=297 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=8.81 (d, 1H), 8.70 (s, 1H), 8.59 (s, 1H), 8.47 (s, 1H), 7.92 (s, 1H), 7.77 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89570-84-3, 2-Hydrazinyl-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1256810-26-0, 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. 1256810-26-0, name is 6-Bromo-3-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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 mixture of 6-bromo-3-methoxypicolinic acid (3.6 g, 15.52 mmol) and K2CO3 (4.29 g, 31 .0 mmol) in A/,A/-Dimethylformamide (20 mL) was added iodomethane (4.40 g, 31 .0 mmol). The reaction mixture was stirred at 60 C for 4h. The mixture was then poured into water (10 mL) and was extracted with EtOAc (3×30 mL). The combined organic layers were washed by aqueous LiCI (2×30 mL) and brine (50 mL), dried over anhydrous MgS04 and concentrated in vacuum to give crude methyl 6-bromo-3-methoxypicolinate as a clourless gum. Ethyl 2- chloro-2,2-difluoroacetate (7.38 g, 46.5 mmol), potassium fluoride (9.01 g, 155 mmol) and copper(l) iodide (8.86 g, 46.5 mmol) and A/,A/-Dimethylformamide (20.00 mL) were then added and the reaction mixture was stirred at 120 C for 18h. The mixture was cooled to rt and water (30 mL) was added. The mixture was filtered and extracted with EtOAc (3×30 mL). The combined organic layers were washed by aqueous LiCI (2×30 mL) and brine (50 mL), dried over anhydrous MgS04 and concentrated in vacuum to give methyl 3-methoxy-6- (trifluoromethyl)picolinate as a crude product. The crude product was dissloved in methanol (20 mL) and a solution of LiOH (1 .858 g, 78 mmol) in water (20 mL) was added. The reaction mixture was stirred at 40 C for 1 h. The pH was then adjusted to 5 with 1 N HCI. The mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous MgS04 and concentrated under vacuum to give 3-methoxy-6- (trifluoromethyl)picolinic acid (1 .7 g, 6.92 mmol, 44.6 % yield) as a white solid, m/z: [M + H]+ Calcd for C8H7F3NO3 222.0; Found 222

According to the analysis of related databases, 1256810-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Diisopropyl azodicarboxylate (9.87 mL, 50.13 mmol) was added to a stirred solution of 4- chloro-5-nitropyridin-2-ol (intermediate 156) (7 g, 40.10 mmol) and triphenylphosphine (15.78 g, 60.16 mmol) in THF (180 mL) under nitrogen. The reaction mixture was stirred at ambient temperature for 10 minutes and then (lr,4r)-methyl 4- hydroxycyclohexanecarboxylate (6.34 g, 40.10 mmol) in THF (45 mL) was added and the resulting solution was stirred at ambient temperature over the weekend. The reaction mixture was evaporated and the residue was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Yielded (ls,4s)-methyl 4-(4-chloro-5- nitropyridin-2-yloxy)cyclohexanecarboxylate (2.86 g, 22.66 %). 1H NMR (400 MHz, DMSO) delta 1.70 – 1.87 (8H, m), 3.61 (3H, s), 5.28 (IH, d), 7.30 (IH, s), 8.96 (IH, s). IH obscured by DMSO peak. No mass ion.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
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. 1072-98-6, name is 2-Amino-5-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5ClN2

PREPARATION 61 2-Amino5-chloro-3-nitropyridine A procedure similar to that described in Preparation 56 was repeated, except that 25.0 g of 2-amino-5-chloropyridine, 100 ml of concentrated sulfuric acid and 12.5 ml of concentrated nitric acid were used, to give 18.5 g of the title compound, melting at 138-139 C.

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, 1072-98-6, 2-Amino-5-chloropyridine.

Reference:
Patent; Sankyo Company, Limited; US5624935; (1997); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-5-chloro-3-nitropyridine

A mixture of 2-bromo-5-chloro-3-nitropyridine (2.8 g; 11.79 mmol) and copper(I) cyanide (1.40 g, 15.63 mmol) in DMF (30 mL)was stirred at 110C for 1.5 h. The mixture was concentrated. The residue was diluted with water (60 mL), extracted three times with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by columnchromatography (elution: DCM/Petroleum ether 1/1). The desired fractions were collected and concentrated to give 1.10 g of intermediate 521 (51% yield) as a yellow solid.

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, 75806-86-9, 2-Bromo-5-chloro-3-nitropyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, 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. 184416-84-0, name is 2,3-Dichloroisonicotinic acid. A new synthetic method of this compound is introduced below.

A.2.5.1 Synthesis of 2,3-dichloroisonicotinic acid ethyl ester To a solution of 2,3-dichloroisonicotinic acid (5.62 mmol) in 15 mL DMF were added NaH (7.31 mmol) followed by iodoethane (6.75 mmol) at 0 C. The cooling bath was removed and the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL from Biotage) using Hept/EtOAc (6/4) gives the desired product as yellow oil; LC-MS (A): tR=0.78 min; [M+H]+: 219.95.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,184416-84-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Hilpert, Kurt; Hubler, Francis; Kimmerlin, Thierry; Renneberg, Dorte; Stamm, Simon; Murphy, Mark; US2014/163035; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem