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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid. A new synthetic method of this compound is introduced below., Product Details of 59290-81-2

ED-14a (1.01 g, 5.52 mmol) is placed in tBuOU (50 mL), combined with DPPA (1.8 mL, 8.35 mmol) and NMM (724 muL, 6.59 mmol) and refluxed for 15 h. After cooling, saturated sodium chloride solution is added and the mixture is extracted several times with EE. The combined organic phases are washed with saturated sodium chloride solution, dried on MgSO4, filtered and evaporated down using the rotary evaporator. The residue is taken up in some water and freeze-dried. The Z-4a thus obtained (HPLC-MS: tRet. = 1.73 min; MS (M+H)+ = 254) is used without further purification.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STEURER, Steffen; ETTMAYER, Peter; MANTOULIDIS, Andreas; WO2010/34838; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, 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, 63237-88-7, blongs to pyridine-derivatives compound. Formula: C8H6N2O2

[00274] A mixture of 0.1 g [1 ,3]thiazolo[5,4-e][1 ,3]benzothiazol-2-amine, 0.094 g pyrazolo[1 ,5-a]pyridine-2-carboxylic acid, 0.275 g HATU, and 0.156 g DIEA were stirred at 50C in 9 mL of dry THF for 8 hours. The mixture was diluted with water and the precipitate was recrystallized from methanol/DMF to yield 0.07 g of N-([1 ,3]thiazolo[5,4-e][1 ,3]benzothiazol-2- yl)pyrazolo[1 ,5-a]pyridine-2-carboxamide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63237-88-7, its application will become more common.

Reference:
Patent; KINEATA INC; Ladonato, Shawn P.; Bedard, Kristin M.; Munoz, Ernesto J.; Imanaka, Myra W.; Fowler, Kerry W.; (122 pag.)WO2014/113492; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 21717-95-3, 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 21717-95-3, name is 2-Amino-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A 25 -mL round-bottomed flask was charged with 3-fluoro-2- pyridinamine (1.0 g 8.9 mmol, Matrix Scientific, USA) and AcOH (10 mL). The reaction mixture was cooled to 0 C and NIS (2.0 g, 8.9 mmol, Sigma-Aldrich, India) was added in portions under a nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was diluted with cold water (30 mL), followed by a mixture of 5% Na2S203 (50 mL) and NaHC03 (100 mL) at room temperature. The solid that formed was collected via filtration, washed thoroughly with water and dried under reduced pressure at 40 C to give 3-f uoro-5-iodo-2-pyridinamine (2.0 g) as a white solid.

According to the analysis of related databases, 21717-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); 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 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (2 g, 6.69 mmol) was suspended in toluene (8 ml), then p-toluenesulfonic acid (TsOH) (0.1 15 g, 0.669 mmol) and acetonylacetone (0.941 ml, 8.03 mmol) was added. The reaction mixture was heated at reflux for 2hrs and allowed to cool to RT overnight. The resulting dark red/ black solution was concentrated in vacuo to remove toluene and the crude residue diluted with 200ml EtOAc, washed with NaHC03 (50 ml), dried (MgS04) and concentrated in vacuo to give a brown solid; LC-MS Rt = 5.58 min [M+H]+ 377/379 (Method 10minl_C_v002). 1 H NMR (400 MHz, DMSO-d6) ? 8.50 (1 H, s), 7.77 (2H, s), 5.83 (3H, s), 1.90 (6H, s); 19F NMR (400 MHz, DMSO-d6) ? -62.26 (CF3, s)

With the rapid development of chemical substances, we look forward to future research findings about 866775-18-0.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUTLER, Rebecca; COLLINGWOOD, Stephen, Paul; HALL, Edward, Charles; EDWARDS, Lee; LEGRAND, Darren, Mark; SPIEGEL, Katrin; WO2013/38386; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 823-39-2, 3,4-Dimethylpyridin-2-amine, 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, 823-39-2, blongs to pyridine-derivatives compound. COA of Formula: C7H10N2

Preparation M (3beta,5alpha,25R)3-trimethylsilyloxy-spirostan-11-one Silylation of Spirostanes Trimethylsilylchloride (3.27 mL, 25.8 mmol) was added to a solution of (3beta,5alpha,25R)3-hydroxy-spirostan-11-one (4.0 g, 9.3 mmol) and triethylamine (6.5 mL, 46 mmol) in dichloromethane (60 mL) at room temperature. One gram of dimethyl aminopyridine was added and the reaction was stirred at room temperature for 12 hours. The reaction was quenched with methanol (1 mL) and diluted with ethyl acetate, washed with water (5*) and brine (1*), dried (Na2 SO4), filtered and concentrated in vacuo. The product was triturated with methanol, filtered and dried to afford 3.94 g (85percent) product as a white solid. 1 H NMR (250 MHz, CDCl3) 6 4.5 (q, 1H, J=6Hz); 3.45 (m, 2H); 2.35 (t, 1H, J=10 Hz); 2.4 (dt, 1H, J=12.2 Hz); 2.2 (s, 2H); 2.1-1.1 (m, 12H); 1.02 (s, 3H); 0.9 (d, 3H, J=7.0 Hz); 0.78 (d, 3H, J=7 Hz); 0.69 (s, 3H); 0.1 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-39-2, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5939398; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, 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, Recommanded Product: 63237-88-7, blongs to pyridine-derivatives compound. Recommanded Product: 63237-88-7

Step (d) N-((ls,4s)-4-(2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)biphenyl-3- yloxyJ-S-fluoronicotinamidoJcyclohexylJpyrazolo [ 1 ,5-a] pyridine-2-carboxamideTo a suspension of N-((ls,4s)-4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l- yl)methyl)biphenyl-3-yloxy)-5-fluoronicotinamide (210 mg, 0.35 mmol) in acetonitrile (4.2 mL) was added pyrazolo[l,5-a]pyridine-2-carboxylic acid (70.4 mg, 0.43 mmol) and triethylamine (484 mul, 3.47 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (277 mul, 0.43 mmol) was then added and the mixture stirred at RT for 2 hours. The mixture was evaporated to dryness and the residue dissolved in DCM (100 mL) and washed with saturated NaHCO3 (aq), brine, dried (MgSO^ and evaporated to give a foam. This was purified by HPLC to give the title compound as a white solid. Yield: 197 mg 1H NMR (400 MHz, CD3OD) delta 8.48 (d, J = 7.2 Hz, IH), 8.39 (d, J = 7.5 Hz, IH), 8.13 (d, J = 3.1 Hz, IH), 8.10 – 8.05 (m, IH), 7.68 – 7.63 (m, IH), 7.58 – 7.55 (m, IH), 7.54 – 7.47 (m, 3H), 7.45 – 7.42 (m, IH), 7.36 – 7.17 (m, 4H), 6.96 – 6.92 (m, 2H), 4.19 – 4.12 (m, IH), 4.04 -3.97 (m, IH), 3.72 (s, 2H), 3.44 – 3.34 (m, 2H), 3.15 – 3.09 (m, 2H), 2.20 (t, J = 12.4 Hz, 2H),1.98 – 1.68 (m, 8H), 1.24 (d, J = 6.7 Hz, 6H). MS: [M+H]+=676 (calc=676) (MultiMode+)

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 578007-66-6, Adding some certain compound to certain chemical reactions, such as: 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine,molecular formula is C6H5BrINO, 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 578007-66-6.

EXAMPLE 119; N-(2-Methoxy-5-(4-morpholinoquinolin-6-yl)pyridin-3- yl)methanesulfonamide; (1) N-(5-Bromo-2-methoxypyridin-3-yl)methanesulfonamide.; To a 5 mL microwave vial, 5-bromo-3-iodo-2-methoxypyridine (0.317 g, 1.01 mmol, Alfa Aesar, Ward Hill, MA), methanesulfonamide (0.100 g, 1.06 mmol), cesium carbonate (0.829 g, 2.54 mmol) and copper(I) iodide (0.0211 g, 0.111 mmol) were mixed into DMF (1 mL). water (0.1 mL) was added and the mixture was heated at 105 0C for 20 h. The reaction mixture was poured into water/Tris-lM HCl pH 7 buffer then IN HCl was added to bring pH to ~5. The aqueous phase was extracted with EtOAc (3 X 20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluent: EtOAc in hexanes 0 % – 50 %) to afford an off white solid (0.135 g) as the desired product. MS (ESI pos. ion) m/z calcd for C7H9BrN2O3S: 280.0; found 280.8/282.8 [M+l/M+3]. 1H NMR (300 MHz, CHLOROFORM-^), delta ppm 3.04 (s, 3 H) 3.92 – 4.07 (m, 3 H) 6.74 (br. s., 1 H) 7.89 (d, J=2.19 Hz, 1 H) 7.97 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 578007-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, 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, Application In Synthesis of 6-Chloro-2-methyl-3-nitropyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Chloro-2-methyl-3-nitropyridine

To the 1-liter autoclave was added 300 ml of ethanol, 86.3 g (0.5 mol) of 6-chloro-3-nitro-2-methylpyridine, 8.6 g of a 5% palladium-carbon catalyst, stirred and heated to 40 ~ 45 , through the high purity hydrogen, maintain the hydrogen pressure 0.3 ~ 0.5MPa, the reaction 6 ~ 8 hours, the sample sampling sample 6-chloro-3-amino-2-methyl pyridine content of less than 0.3% The reaction was carried out at room temperature and the catalyst was filtered off and the resulting filtrate was evaporated to dryness under reduced pressure to give a gray solid which was recrystallized from a mixed solution of ethyl acetate and cyclohexane to give 56.1 g of product and a relative liquid content of 98% , Which can be used directly for the further reaction of Example 2 below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Xihua University; Yang, WeiQing; Zou, Hao; zhang, yuanyuan; Huang, JiHong; Ren, chuanhong; (5 pag.)CN104003934; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 717843-56-6, 3-Bromo-2-methoxy-5-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, Application In Synthesis of 3-Bromo-2-methoxy-5-methylpyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Bromo-2-methoxy-5-methylpyridine

Step b: 2-Methoxy-5-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridine; 3-Bromo-2-methoxy-5-methylpyridine (540 mg, 2.7 mmol), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(l,3,2-dioxaborolane) (810 mg, 3.2 mmol), and Pd(dppf)Cl2 (110 mg, 0.13 mmol) were added to a dry flask and placed under N2. Potassium acetate (800 mg, 8.1 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (DMF) (15 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield 2-methoxy-5- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (450 mg, 67%). ESI-MS m/z calc. 249.1, found 168.3 (MW-C6H1O+1)+. Retention time 0.27 minutes. 1H nuMR (400 MHz, CDCl3) delta 8.03 (m, IH), 7.80 (m, IH), 3.94 (s, 3H), 2.22 (s, 3H), 1.36 (s, 12H).

The synthetic route of 717843-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1211521-46-8 ,Some common heterocyclic compound, 1211521-46-8, molecular formula is C6H5BrClN, 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.

A solution of 2-bromo-3-methyl-4-chloro-pyridine (10.6 g, 57.1 mmol) in freshly distilled THF (120 mL) was cooled down to 0C and treated with isopropyl magnesium chloride (45.7 ml_, 2.0 M in THF, 91 .5 mmol). The resulting mixture was stirred at room temperature for 3 h then cooled to -5C. Cyclopropane carboxaldehyde (6.83 mL, 91 .5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and quenched by adding water (100 mL), and extracted with ethyl acetate (2X150 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1 ) to afford the title compound as a yellow oil (7.01 g, 62%).ESI-MS m/z: 198 (M+H)+; 1H NMR (CDCI3, 300 MHz) delta ppm: 8.28 (d, J= 5.4 Hz, 1 H), 7.26 (d, J = 5.4 Hz, 1 H), 4.79 (d, J = 5.4 Hz, 1 H), 4.55 (br s, 1 H), 2.39 (s, 3 H), 1 .10-1 .28 (m, 1 H), 0.41 -0.58 (m, 4 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. 1211521-46-8, 2-Bromo-4-chloro-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EVOLVA SA; HEIM, Jutta; SCHNEIDER, Peter; ROUSSEL, Patrick; MILLIGAN, Daniel; WO2012/104305; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem