Month: April 2022

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

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

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: 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

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

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

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

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

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

Related Products of 917760-91-9, 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 917760-91-9, name is 3-(5-Fluoropyridin-2-yl)acrylic acid hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 10b (E)-3-(5-fluoropyridin-2-yl)acrylic acid methyl ester A mixture of (E)-3-(5-fluoropyridin-2-yl)acrylic acid hydrochloride (10 g), sulfuric acid (2.0 mL) and methanol was stirred at room temperature for 17 hours and then at 50 C. for 4 hours. The mixture was cooled to 0 C. and the pH of the solution adjusted to 8-9 by the addition of 1.0 M aqueous sodium hydroxide solution. The resulting precipitate was collected by filtration, washed with water and dried to afford title compound as a white solid, 9.0 g. 1H NMR (DMSO-d6): delta 3.75 (s, 3H), 6.85 (dd, J=0.6, 15.7 Hz, 1H), 7.70 (d, J=15.7 Hz, 1H), 7.80-7.90 (m, 2H), 8.65 (d, J=2.9 Hz, 1H). MS: ESI (+ve) (Method B): 182 (M+H)+, Retention time 2.8 min.

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 917760-91-9, 3-(5-Fluoropyridin-2-yl)acrylic acid hydrochloride.

Reference:
Patent; Hynd, George; Ray, Nicholas Charles; Finch, Harry; Middlemiss, David; Cramp, Michael Colin; Blaney, Paul Matthew; Williams, Karen; Griffon, Yan; Harrison, Trevor Keith; Crackett, Peter; US2009/163534; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem