Pyridine-derivatives

Electric Literature of 586-98-1, 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 586-98-1 as follows.

[Methanesulfonic acid pyridin-2-y I methyl ester] (11) To a solution of 2-pyridylcarbinol (10) (300 mg, 2.70 mmol) and triethyl amine (698 mg, 6.75 mmol) in dry THF (10 ml_) at O0C was added a solution of mesylchloride (470 mg, 4.1 mmol) in dry THF (10 ml_). Reaction mixture was allowed to stir for 2 h at room temperature [reaction was followed by TLC]. Reaction mixture was concentrated to remove THF under reduced pressure and the residue was dissolved in CH2CI2 (100 ml_), washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give compound 11 (300 mg, 59%) as gum and it was taken as such for next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,586-98-1, its application will become more common.

Reference:
Patent; NEUROSEARCH A/S; WO2007/42545; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-11-1, Methyl 2-chloroisonicotinate, 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, name: Methyl 2-chloroisonicotinate, blongs to pyridine-derivatives compound. name: Methyl 2-chloroisonicotinate

In a dried flask was zinc powder (0.769 g, 11.76 mmol) suspended in anhydrous tetrahydrofuran (20 mL) under nitrogen. The resulting suspension was warmed to 60¡ã C., then 1,2-dibromoethane (0.042 mL, 0.49 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.050 mL, 0.39 mmol) was added and stirred at room temperature for 1 h. Then, 1-(bromomethyl)-4-(trifluoromethoxy)benzene (2.5 g, 9.80 mmol) in tetrahydrofuran (5 mL) was added over 2 min, then stirring continued at room temperature for 22 h. The stirring was switched off to let the solids settle. The supernatant was used in next transformation. To a solution of methyl 2-chloroisonicotinate (4.80 g, 28 mmol) and Pd(PPh3)4 (0.647 g, 0.56 mmol) in tetrahydrofuran (50 mL) under nitrogen in a dried flask was added a freshly prepared solution of (4-(trifluoromethoxy)benzyl)zinc(II) bromide (12.56 g, 39.20 mmol) in tetrahydrofuran (90 mL). The resulting bright yellow mixture was heated to 60¡ã C. for 2 h 30 min, then cooled to room temperature. The reaction was quenched by the addition of 10percent aqueous NH4Cl. It was diluted with ethyl acetate. After phase separation, the organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was suspended in 50 mL MTBE and sonicated, then the yellow insolubles were filtered off and washed with MTBE. The volume of the filtrate was increased to ca. 150 mL, then 5 mL MeOH was added, followed by hydrogen chloride (4 M in dioxane) (7.00 mL, 28.00 mmol). A colorless precipitate formed, which then dissolved again. The solvents were evaporated. The residue was dissolved in ca. 15 mL DCM and then MTBE and heptanes were added. An oil had formed that was triturated and after a few minutes a solid started to form. It was sonicated and then stirred at room temperature for 20 min. The formed solid was collected and washed with MTBE and dried. The solid was dissolved in DCM and washed with 10percent K2CO3. After phase separation, the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(4-(trifluoromethoxy)benzyl)isonicotinate (8.04 g, 92percent) was isolated as a pale yellow oil. 1H NMR (400 MHz, cdcl3) delta 3.93 (s, 3H), 4.22 (s, 2H), 7.11-7.17 (m, 2H), 7.24-7.31 (m, 2H), 7.67-7.72 (m, 2H), 8.68-8.72 (m, 1H). MS m/z 312 (M+H)+

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; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59864-31-2, Adding some certain compound to certain chemical reactions, such as: 59864-31-2, name is 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid,molecular formula is C7H7NO3, 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 59864-31-2.

620 mg (3.7 mmol, 1 equiv.) of 1-methyl-6-oxo-1 ,6-dihydro-pyridine-2-carboxylic acid were dissolved in 5 mL of dry dichloromethane and to it DIPEA (3 equiv.) and HATU (1 equiv.) were added. After 10 min stirring at 0 ¡ãC, (4-fluorophenyl)-hydrazine hydrochloride (1.5 equiv.) was added. The reaction mixture was allowed to stir overnight at room temperature under nitrogen atmosphere. After the completion of the reaction, solvent was removed and the residue was washed with brine (two times, 5 mL) and extracted with dichloromethane (three times, 10ml_). The collected organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography to obtain 200 mg of pure title compound (19percent). 1H NMR (500 MHz, CDCI3) delta: 3.4 (s, 3H), 4.39 – 4.44 (m, 2H), 6.49 – 6.50 (m, 1 H), 6.55 – 6.57 (m, 1 H), 6.82 – 6.85 (m, 2H), 7.02 – 7.06 (m, 2H), 7.48 – 7.50 (m, 1 H), 10.62 (s, 1 H); Signal of a NH proton was not observed; LC-MS: 262.2 (M+H); Purity (HPLC): 94.44 percent

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. 59864-31-2, 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FERRER INTERNACIONAL, S.A.; GARGALLO VIOLA, Domingo; PALOMER BENET, Albert; (85 pag.)WO2016/16291; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69045-84-7, 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. 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

A mixture of 2,3-dichloro-5-(trifluoromethyl)pyridine (10 mL, 72 mmol), hydrazine (10 mL, 0.32 mol), and ethanol (100 mL) was refluxed for 4 h, allowed to cool to rt, and then concentrated. The residue was partitioned between EtOAc (100 mL) and 0.43M NaOH (175 mL). The organic layer was dried, filtered, concentrated, and dried under vacuum to give 3-chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine as an off- white solid. 1H NMR (400 MHz, DMSO-d6): delta 8.53 (s, IH), 8.35 (d, IH), 7.91 (d, IH), 4.43 (s, 2H); LCMS: 212.3 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-84-7, its application will become more common.

Reference:
Patent; KALYPSYS, INC.; WO2009/117421; (2009); A2;,
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.98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.HPLC of Formula: C6H7BrN2

Nitric acid (0.7 ml) was added dropwise to a solution of 5-bromo-4-methylpyridine-2-amine (2.0 g) in concentrated sulfuric acid (8.7 ml) at 55 C. over 30 minutes, and the mixture was stirred at the same temperature for 3 hours. After further stirring at room temperature for 2 hours, the reaction solution was poured into ice water. A 50% aqueous sodium hydroxide solution was added, and the resulting precipitate was collected by filtration, washed with distilled water and then dried under reduced pressure to give the title compound (2.5 g).MS (ESI) m/z: 268 (M+H)+.1H-NMR (CDCl3) delta: 2.54 (3H, s), 5.83 (2H, brs), 8.29 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98198-48-2, 2-Amino-5-bromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13958-98-0, 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. 13958-98-0, name is 3-Bromo-4-cyanopyridine, molecular formula is C6H3BrN2, 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.

1008741 Step C: Preparation of 3-cyclobutylisonicotinonitrile: Charged a dry round bottomed flask plus stir bar with 3-bromoisonicotinonitrile (6.1 g, 33 mmol), anhydrous THF (150 mL), dicyclohexyl(2?,6?-dimethoxy-[ 1,1 ?-biphenyl] -2-yl)phosphine ?S-Phos? (1.0 g, 2.5 mmol), and Pd(OAc)2 (0.37 g, 1.7 mmol). Purged the reaction mixture with N2. Added cyclobutylzinc(II) bromide (100 mL, 50 mmol; 0.5 M in THF) over 15 minutes via cannula. Stirred the reaction mixture for 2 hours at ambient temperature. Partioned mixture between EtOAc (200 mE) and water (200 mE), and filtered through Celite to remove insoluble solids, rinsing with EtOAc. Separated phases, and re-extracted aqueous phase with EtOAc (100 mL). The combined organic phases were washed with brine (150 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by Biotage Flash 65 silica gel column, eluting with a gradient of 10% EtOAc/hexanes to 1:1 EtOAc/hexanes. Yield: 2.3 g (43%).

According to the analysis of related databases, 13958-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BRANDHUBER, Barbara J.; HAAS, Julia; NEWHOUSE, Brad; THOMAS, Allen A.; WINSKI, Shannon L.; WO2014/78331; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 947249-14-1, 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.947249-14-1, name is 3-(Difluoromethoxy)pyridin-2-amine, molecular formula is C6H6F2N2O, molecular weight is 160.1215, as common compound, the synthetic route is as follows.

To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 mL) was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 mm at 0 C. The reaction mixture was stirred at the same temperature for another 20 mm and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were driedover sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20% ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93%): 1H NMR (400 MHz, DMSO-d6) oe: 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, I = 73.6 Hz, 1H), 6.34 (s, 2H).

Statistics shows that 947249-14-1 is playing an increasingly important role. we look forward to future research findings about 3-(Difluoromethoxy)pyridin-2-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); 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. 10201-73-7, name is 2-Amino-4-methoxypyridine, the common compound, a new synthetic route is introduced below. name: 2-Amino-4-methoxypyridine

2-Amino-4-methoxypyridine (1.24 g, 10 mmol) was dissolved in 100 mL of acetic acid, After cooling to 0 degrees, A solution of bromine (1.92 g, 12 mmol) in acetic acid (30 mL) was added dropwise. Dropping is completed, The solution is reacted at 30 degrees. 4h, TLC monitoring raw material has been completely reacted, To the reaction solution was added 40 mL of saturated aqueous sodium sulfite solution, 25 degrees stirring reaction 0.5h, Concentrated under reduced pressure, The residue was extracted with ethyl acetate (150 mL ¡Á 3) Dried over anhydrous sodium sulfate, filter, The filtrate was concentrated under reduced pressure, Column chromatography (V (methylene chloride) / V (methanol) = 20/1), Obtained as a light yellow solid (1.45 g, 73%).

The synthetic route of 10201-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Zhen, Changchun; Liu, Bing; Zhang, Weihong; Zhang, Yingjun; Long, Bohua; (59 pag.)CN104513257; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 122307-41-9 , The common heterocyclic compound, 122307-41-9, name is 4-Chloro-3-methoxy-2-methylpyridine 1-oxide, molecular formula is C7H8ClNO2, 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.

b 2-Methyl-3-methoxy-4-(2,2,2-trifluoroethoxy)pyridine N-oxide 6.7 g of potassium tert-butoxide were added in portions, at -20 C., while stirring and under a nitrogen atmosphere, 5 to 20 ml of trifluoroethanol. After the mixture had been warmed to 0 C., 5.2 g (30 mmol) of 2-methyl-3-methoxy-4-chloropyridine N-oxide were added in portions. The mixture was heated under reflux for 3 hours, and then left to cool down to room temperature; a further 3.45 g of potassium tert-butoxide were then added and the mixture was heated under reflux for 2 hours. After it had cooled down, 40 ml of water were added to the reaction mixture, which was then extracted with dichloromethane; the extract was then dried over MgSO4 and freed from the solvent in vacuo. The resulting oily product was subjected to further reaction.

The synthetic route of 122307-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US5658933; (1997); 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. 93349-99-6, name is Methyl 5-bromo-6-methoxynicotinate. A new synthetic method of this compound is introduced below., Product Details of 93349-99-6

26B: A mixture of 1A (378 mg, 0.915 mmol), bis(pinacolato)diboron (290 mg,1.143 mmol), potassium acetate (269 mg, 2.74 mmol) and PdC12(dppf)-CH2C12 adduct (37.3 mg, 0.046 mmol) in dioxane (4 mL) was heated at 100 C for 60 mm. After cooling to rt, methyl 5-bromo-6-methoxynicotinate (154 mg, 0.625 mmol) and1,1 ?-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (19.39 mg, 0.030 mmol) were added and the mixture degassed by nitrogen sparge for 5 mm. 2M K3P04 (aq) (0.892 mL, 1.785 mmol) was quickly added and the reaction mixture heated at 100 C for 15 mm. The reaction mixture was cooled to rt and volatiles removed in vacuo. The crude residue was loaded onto a 40g ISCO column and purified by flash chromatography,eluting with 0-100% EtOAc in hexanes. Afforded product (301 mg, 0.572 mmol, 96 % yield) as a crystalline beige solid.MS ESI m/z 499.9 (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, 93349-99-6, Methyl 5-bromo-6-methoxynicotinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem