Pyridine-derivatives

Application of 20511-12-0, 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 20511-12-0, name is 5-Iodopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 m was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40C at reduced pressure and the residue was purified by column chromatography (silica gel, 200 – 300 mesh, ethyl acetate / petroleum ether 3: 1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47 %) as a yellow solid. 1H NMR (300MHz, DMSO): delta 8.07 (s, 1H), 7.98 – 7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.

According to the analysis of related databases, 20511-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; PADILLA, Fernando; WANNER, Jutta; XIE, Wenwei; ZHANG, Xiaohu; WO2012/163724; (2012); 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-5-methoxypyridine

To a 14 mL test tube equipped with a stir bar was added (S)-(5-(1-(tert-butoxy)-2-isopropoxy-2-oxoethyl)-4-(4,4-dimethylpiperidin- 1 -yl)-6-methylpyridin-3 -yl)boronic acid(105 mg, 0.250 mmol), SPhos-Pd-G3 (9.73 mg, 0.0 12 mmol), tribasic potassium phosphate (477 mg, 2.248 mmol) and 2-chloro-5-methoxypyridine (35.9 mg, 0.250 mmol) . The flask was sealed with a rubber septum, then was placed under N2 atm (vac/fill x 3). To the flask was added degassed (N2 bubbling for 5 mm) dioxane (937 .il) and water (312 .il) . The test tube was placed in a 60 C heating block with stirring (t=0). The reaction was stirred for 3 hours. The reaction was cooled to RT and diluted withwater and EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, filtered and hte volatiles evaporated to afford the cmde product. The crude product was purified on silica gel (24 g column, 20-100% EtOAc:Hex) to afford the product isopropyl (S)-2-(tert-butoxy)-2-(4?-(4,4-dimethylpiperidin- 1 -yl)-5 -methoxy-6?-methyl-[2,3 bipyridinj-5?-yl)acetate (22 mg, 0.045 mmol, 18.21 % yield) as a brown oil. ESI-MS(+)m/z = 484.3 (M+1).

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 42373-30-8, 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 42373-30-8, name is 4-Aminonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCI (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgS04 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99 %).

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 42373-30-8, 4-Aminonicotinaldehyde.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188057-20-7, 4-Iodopyridin-3-ol, 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: 4-Iodopyridin-3-ol, blongs to pyridine-derivatives compound. Recommanded Product: 4-Iodopyridin-3-ol

Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[2,3-c]-2-boronic acid (14): Prepared from 3-hydroxy-4-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 262.4 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder. The mixture was treated with hot EtOH to afford 14 (216.4 mg, 66%) as a pale yellowsolid; IR (cm-1) 3006, 1734, 1683, 1608, 1473, 1373, 1322, 1259, 1216, 1159, 1093, 1016; 1H-NMR(DMSO-d6) delta 7.50 (d, J = 1.0 Hz, 1H), 7.74 (dd, J = 1.0 Hz, 5.0 Hz, 1H), 8.37 (d, J = 5.0 Hz, 1H), 8.96(brs, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0514 (Delta 0.07).

The synthetic route of 188057-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116355-18-1, 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below.

EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116355-18-1, 6-Bromo-7-methylimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5832-43-9, 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 5832-43-9, name is 4-Methyl-5-nitropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 4-methyl -5-nitropicol i nateTo a solution of 4-methyl-5-nitropicolinic acid (5.0 g, 27.5 mmol) in methanol (60 mL) was slowly added concentrated sulfuric acid (4.39 mL, 82 mmol) and the mixture was refluxed under argon for 18 h. The volatiles were evaporated and a sat. aq. solution of NaHCO3 was added slowly until the aqueous phase showed a pH of 7-8. The resultant mixture was extracted with CH2CI2 (x3), the combined organic extracts were dried (phase separator) and concentrated under vacuum. MS (UPLC-MS): 197.0 [M+H]+, tR (HPLC conditions h): 1.99 mm.

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 5832-43-9, 4-Methyl-5-nitropicolinic acid.

Reference:
Patent; NOVARTIS AG; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; RANDL, Stefan Andreas; VULPETTI, Anna; WO2014/2057; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 823221-93-8 ,Some common heterocyclic compound, 823221-93-8, molecular formula is C6H2BrClF3N, 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 mixture of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (commercially available) (75 mg, 0.288mmol), 2,2-dimethylpropanamide (32 mg, 0.317 mmol), XantPhos Pd G3 precatalyst (13 mg,0.0 14 mmol), K2C03 (79 mg, 0.57 mmol) in 1 ,4-Dioxane (0.5 mL) was heated at 90C for 0.5hand then 110C for 2h. Purification by reverse phase HPLC delivered product (14 mg, 15%). LC-MS: (positive ES MH+ 281).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823221-93-8, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PHADTE, Mangala; SONAWANE, Ravindra; HENNESSY, Alan Joseph; MORRIS, James Alan; BOEHMER, Jutta Elisabeth; DESSON, Timothy Robert; GOODWIN-TINDALL, Jake; WO2015/59262; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 914358-72-8 ,Some common heterocyclic compound, 914358-72-8, 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.

Example 60(1r,4r)-6′-(5-Chloro-6-methylpyridin-3-yl)-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (287 mg, 1.13 mmol), (1r,4r)-6′-bromo-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (Example 19, 213 mg, 0.57 mmol) and potassium acetate (167 mg, 1.70 mmol) and dioxane (3 mL) were added and the mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 (32.4 mg, 0.04 mmol) was added and the mixture was heated to reflux for 1.5 h under N2 atmosphere. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (120 mg, 0.47 mmol) was added and the reaction was heated to reflux overnight. The volatiles were removed in vacuo and 80 mg of the residue ((1r,4r)-4-methoxy-5”-methyl-6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (MS (ES+) m/z 424 [M+H]+) was mixed with 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 47 mg, 0.23 mmol), K2CO3 (0.38 mL, 0.76 mmol) and dioxane (2 mL). The mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 adduct (138 mg, 0.19 mmol) was added. The vial was sealed and heated in a microwave reactor at 140 C. for 30 min. EtOAc was added and the mixture was washed with brine and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (12 g SiO2, 0-20% MeOH containing 0.1 M NH3 in DCM). The crude product was purified with preparative chromatography. The fractions containing product were combined and concentrated. The water phase was extracted with DCM and the phases were separated using a phase separator. The organic phase was concentrated in vacuo yielding the title compound (5 mg, 6% yield): 1H NMR (CD3OD) delta ppm 1.11 (td, 1H), 1.24-1.43 (m, 2H), 1.49 (td, 1H), 1.63 (td, 2H), 1.90-2.00 (m, 2H), 2.32 (s, 3H), 2.61 (s, 3H), 3.04-3.12 (m, 1H), 3.15 (d, 1H), 3.25 (d, 1H), 3.33 (s, 3H), 6.99 (d, 1H), 7.47 (d, 1H), 7.55 (dd, 1H), 7.99 (d, 1 H), 8.51 (d, 1H); MS (MM-ES+APCI)+ m/z 423 [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,914358-72-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19346-43-1, 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. 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, 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.

18. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid, melting at 63-64 C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDC13): 1 H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13 C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

According to the analysis of related databases, 19346-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DowElanco; US5602075; (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. 6945-67-1, name is 2-Bromo-4-nitropyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-4-nitropyridine

EXAMPLE 47 To a suspension of 2-bromo-4-nitropyridine (406 mg), 3-aminophenylboronic acid (403 mg) and tetrakis(triphenylphosphine)-palladium (116 mg) in 1,2-dimethoxyethane (10 ml) was added 2M aqueous solution of sodium carbonate (2.6 ml). The mixture was stirred at 80 C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give crude 3-(4-nitropyridin-2-yl)aniline. This compound was used for next step without 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, 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem