Category: pyridine-derivatives

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. 1214336-41-0, name is Methyl 5-bromo-3-chloropicolinate, the common compound, a new synthetic route is introduced below. Computed Properties of C7H5BrClNO2

NaBH4 (18.24g, 480.Ommol) was added portion wise to a stirred solution of methyl 5-bromo-3-chloro-picolinate (20g, 80.Ommol) in dry THF (200mL) and MeOH (200m1) at 0C and stirred for 6 h at RT. TheRM was slowly quenched with water (500mL) and extracted with EtOAc (3x200mL). The organic layerwas washed with brine (300mL),then dried (Na2SO4), filtered and evaporated the solvent in vacuo to give(5-bromo-3-choropyridin-2-yl)methanol (16g,crude), as a thick liquid. The crude was taken into next step.

The synthetic route of 1214336-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 92992-85-3, 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 92992-85-3 as follows.

To 2-bromo-3,5-dimethylpyridine (204 muL) were added (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (350 muL),tris(dibenzylideneacetone)dipalladium(0)(73.8 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (100.4 mg),tert-butoxy sodium (232.4 mg) and toluene (4 mL) and the mixture was stirred at 120c for 7 hr. The reaction mixture was cooled and filtered through celite. The filtrate was concentrated and the obtained residue was purified by column chromatography (hexane:ethyl acetate)to give the title compound (459 mg). MS(APCI)m/z:292 (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,92992-85-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); 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 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 23-1 (O.lg, 0.7mmol) in EtOH (15ml) in a dried flask was added Pt2O (O. Ig, 0.4mmol). The reaction mixture was placed under a nitrogen atmosphere and was subsequently evacuated. This was repeated 3 times before placing the reaction mixture under an atmosphere of hydrogen. After 3h the reaction mixture was filtered through celite. Upon solvent removal the desired product 23-2 was obtained as an off-white powder. MS calculated M+H: 167.2, found 167.1

With the rapid development of chemical substances, we look forward to future research findings about 64951-08-2.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
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 10273-89-9, name is 2-(o-tolyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(o-tolyl)pyridine

General procedure: A 10 mL Schlenk tube was charged with CoBr2 (6.6 mg, 0.03mmol), 1,3-diisopropyl-1H-benzimidazol-3-ium bromide (L4; 8.5mg, 0.03 mmol), 4-methoxy-N-[(1E)-1-phenylethylidene]aniline(1a, 67.6 mg, 0.30 mmol), 1-chlorooctane (2a, 76.5 muL, 0.45 mmol), and THF (0.69 mL). A 1.92 M solution of t-BuCH2MgBr inTHF (0.31 mL, 0.60 mmol) was added dropwise at 0 C, and themixture was stirred at r.t. for 6 h. The reaction was quenched by theaddition of 3 M aq HCl (1.0 mL), and the mixture was stirred at r.t.for 1 h, then extracted with EtOAc (3 × 10 mL). The organic layerswere combined, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by chromatography [silicagel, hexane-EtOAc (40:1)].

With the rapid development of chemical substances, we look forward to future research findings about 10273-89-9.

Reference:
Article; Gao, Ke; Yamakawa, Takeshi; Yoshikai, Naohiko; Synthesis; vol. 46; 15; (2014); p. 2024 – 2039;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 33252-28-7, 6-Chloronicotinonitrile, 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, Product Details of 33252-28-7, blongs to pyridine-derivatives compound. Product Details of 33252-28-7

6-(5-methyl-1H-1,2,4-triazol-1-yl)pyridine-3-carboxylic acid 2-Chloro-5-cyanopyridine (1.5 g) is dissolved in hydrazine (6 mL) at r.t. and an exothermic reaction occurs and a solid precipitate forms. Water is added and the solid is filtered off washing with water and is dried by suction to give the hydrazine intermediate. The hydrazine is suspended in acetic acid (7 mL) and N-((dimethylamino)methylene)acetamide [made from acetamide and DMF-dimethylacetal by procedure in US2007/0111984A1] (700 mg) is added and heated at 90 C. for 5.5 h. Additional N-((dimethylamino)methylene)acetamide (200 mg) is added and the mixture is heated at 90 C. for 3 h. After cooling and concentrating the residue is purified by chromatography on silica gel eluting with 0% to 100% ethyl acetate/hexane to give the intermediate nitrile. The nitrile is dissolved in MeOH (10 mL) and 4 M NaOH (2 mL) is added and heated at 65 C. for 16 h. The mixture is neutralized with 6 M HCl, concentrated, and then acidified to pH 2 with 6 M HCl. The precipitate is filtered off washing with water and dried by suction to give the title compound. LC (method 20): tR=1.53 min; Mass spectrum (APCI): m/z=205 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/143892; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59942-87-9 ,Some common heterocyclic compound, 59942-87-9, molecular formula is C7H6N2O, 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 13: Synthesis of 4-(2-(pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine To a solution of pyrazolo[1 ,5-a]pyridin-2-ol (120 mg, 0.89 mmol) in 4 ml_ of anhydrous DMF, were added K2C03 (270 mg, 1 .95 mmol), 4-(2-chloroethyl)morpholine hydrochloride (183 mg, 0.98 mmol) and Nal (134 mg, 0.89 mmol) and the mixture heated to 80 5C for 18 h under nitrogen. The solvent was evaporated under reduced pressure and the residue poured into a mixture of EtOAc and water, to afford after drying and evaporation of organic layers, 1 12 mg of an oil that was purified by silica gel flash chromatography with EtOAc/MeOH (9:1 ) as eluent to afford 57 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine. 40 mg (0.43 mmol) of anhydrous oxalic acid in 0.5 ml_ of acetone were added to a solution of 98 mg of 4-(2- (pyrazolo[1 ,5-a]pyridin-2-yloxy)ethyl)morpholine base oil in 0.5 ml_ of acetone. The solid is filtered and washed with diethyl ether to give 133 mg (90%). 1 H NMR (DMSO) delta ppm: 8.46 (d, J = 6.9 Hz, 1 H), 7.46 (d, J = 8.9 Hz, 1 H), 7.26 – 7.09 (m, 1 H), 6.74 (td, J = 6.9, 1 .4 Hz, 1 H), 6.00 (s, 1 H), 4.41 (t, J = 5.3 Hz, 2H), 3.74 – 3.60 (m, 4H), 3.07 (t, J = 5.2 Hz, 2H), 2.92 – 2.66 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59942-87-9, its application will become more common.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13958-93-5 ,Some common heterocyclic compound, 13958-93-5, molecular formula is C6H3Cl2NO2, 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 8 difluorocyclobutanecarboxamide.2HCI; 3,5-Dichloroiso?icotinic acid (84mg, 0.4mmol), the compound of Preparation 42 (150mg, 0.3mmol), 3- (diethoxyphosphoryloxy)-1 ,2,3-benzotriazin-4(3H)-one (132mg, 0.4mmol) and triethylamine (0.16mL, 1.2mmol) were dissolved in dichloromethane and stirred at room temperature for 24hours. The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and extracted using dichloromethane. The combined organic extracts were concentrated in vacuo to give the crude product. The crude mixture was purified by column chromatography on silica gel using dichloromethane-.methanol EPO (100:0 to 90:10) as eluent. The resulting product was then dissolved in dichloromethane (5mL) and treated with 2M hydrochloric acid in diethyl ether (5mL), the solvents were removed in vacuo to give 43mg of title compound as a white solid.1H NMR (400MHz CDCI3) delta 0.95 (3H, s), 1.20-1.85 (9H, m), 1.85-2.00 (1 H, m), 2.05-2.30 (2H, m), 2.45(1 H, bs), 2.70-3.10 (6H, m), 3.25-3.50 (2H, m), 4.05-4.20 (1H, m), 4.40-4.65 (2H, m), 7.10-7.40 (5H1 m),8.50 (2H, bs).LRMS: m/z APCI+579[MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-93-5, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/77499; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59290-81-2, Adding some certain compound to certain chemical reactions, such as: 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid,molecular formula is C7H6N2O4, 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 59290-81-2.

Compound D5 (208g, 1.15mol) was dissolved in t-butanol (2.1L), and thereto were added DPPA (37OmL) and TEA (223mL). The mixture was heated under reflux overnight, quenched by the addition of brine (10OmL). The resulting mixture was extracted by EA (1.0L) for three times. The combined organic phase was washed with brine (10OmL), dried over anhydrous MgSO4 and concentrated under vacuo. The residue was purified by column chromatography (EA : PE=I :2) to provide compound D6 (1 14.5g, 40% yield) as yellow solid. IH NMR (CDC13, 300MHz): delta=l .54 (s, 9H), 2.60 (s, 3H), 6.53 (s, IH), 8.98-8.99 (d, IH), 9.09-9.10 (d, IH). LC-MS [M+l] +: 252.0.

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. 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); 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. 120422-90-4, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[4,3-c]pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of Intermediate 4 (33 mg, 0.163 mmol) and cyclohexylamine (19 muIota, 0.163 mmol) in n-butanol (1 ml) was stirred at rt overnight, monitoring the reaction by LC/MS. The mixture was heated to 100C overnight and more cyclohexylamine (57 muIota, 0.499 mmol) was added and stirring was continued at 100C overnight. The mixture was then diluted with ethyl acetate and washed with water and brine. The organic phase was dried and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 2:1 petrol-ethyl acetate to give an off-white coloured solid (10 mg, 23%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.13 – 1.25 (m, 1 H), 1.28 – 1.47 (m, 4 H), 1.58 – 1.66 (m, 1 H), 1.69 – 1.79 (m, 2 H), 1.90 – 1.97 (m, 2 H), 2.56 (s, 3 H), 3.91 – 4.01 (m, 1 H), 5.85 (d, J=7.8 Hz, 1 H), 6.56 (s, 1 H). m/z (ES+APCI)+ : 265/267 [M+H]+

The synthetic route of 120422-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; CHAN, Brayn; ESTRADA, Anthony; SWEENEY, Zachary; MCIVER, Edward Giles; WO2011/141756; (2011); A1;,
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. 851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

An eighth exemplary Intermediate D, Intermediate D-8, may be used to synthesize compounds of formula I, wherein R1 is heteroaryl substituted with two R4 substituents. To a solution of //-butyllithium (2.50 M, 1.80 mL, 1.00 equiv) was added dropwise over one min to i- PrMgCl (2.00 M, 1.12 mL, 0.500 equiv) in THF (12 mL) at 0 C under a nitrogen atmosphere. The mixture was stirred at 0 C for 5 min followed by the addition of 5-bromo-4-chloro-2- methoxy-pyridine (1.00 g, 4.50 mmol, 1.00 equiv) after which the mixture was stirred at 0 C for 45 min. To this solution was added 2-isopropoxy-4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolane (836 mg, 4.50 mmol, 917 uL, 1.00 equiv) and the mixture stirred for an additional 15 min prior to stirring at 20 C for 3 h. The reaction mixture was quenched by the addition of satd aq ammonium chloride (20.0 mL) at 20 C and was extracted with ethyl acetate (20.0 mL x 3). The combined organic layers were washed with brine (10.0 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 4-chloro-2-methoxy-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridine (1.00 g, 3.71 mmol, 82.5% yield) as a gray solid, which used for the next step without further purification. 1H NMR (400 MHz, CDCl3) d = 8.47 (s, 1H), 6.77 (s, 1H), 3.97 (s, 3H), 1.38 (s, 12H).

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, 851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem