Pyridine-derivatives

Reference of 343781-36-2, 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 343781-36-2, name is 2,4-Dichloro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4a2 (201 g, 734 mmol) and NaOMe (51.5 g, 954 mmol) in MeOH (2 L) is stirred at RT overnight then heated at 45 C for 3 h. The reaction is diluted with EtOAc, washed with water, brine, dried over MgS04, filtered and concentrated under vacuum. Upon standing crystals are formed. These are collected, washed with a small amount of (/-Pr)20 followed by heptane and dried on a stream of air to afford 4a3.

According to the analysis of related databases, 343781-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; STAMMERS, Timothy; BARBEAU, Xavier; BEAULIEU, Pierre; BERTRAND-LAPERLE, Megan; BROCHU, Christian; EDWARDS, Paul, J.; FORGIONE, Pasquale; GODBOUT, Cedrickx; HUCKE, Oliver; JOLY, Marc-Andre; LANDRY, Serge; LEPAGE, Olivier; NAUD, Julie; PESANT, Marc; POIRIER, Martin; POIRIER, Maude; THAVONEKHAM, Bounkham; WO2011/32277; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 36953-37-4, name is 4-Bromopyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H4BrNO

Step 1. 4-Bromo-2-(difluoromethoxy)pyridine. To a stirring solution of 2-chloro-2,2-difluoroacetate (6.00 g, 39.4 mmol) in ACN (200 mL) was added 4-bromopyridin-2(1H)-one (4.90 g, 28.1 mmol). The mixture was refluxed for 8 h. The resulting mixture was filtered and the filtrate was extracted with hexane (6*20 mL). The combined organic layers were dried (Na2SO4), and concentrated at room temperature to give the title compound as a liquid (2.60 g, 42% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.19-8.20 (s, 1H), 7.48 (s, 1H), 7.52 (s, 1H), 7.54-7.88 (m, 1H).

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, 36953-37-4, 4-Bromopyridin-2(1H)-one.

Reference:
Patent; Bollu, Venkataiah; Breitenbucher, James; Kaplan, Alan; Lemus, Robert; Lindstrom, Andrew; Vickers, Troy; Wilson, Mark E.; Zapf, James; US2014/275531; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6318-51-0 ,Some common heterocyclic compound, 6318-51-0, molecular formula is C12H8ClNO, 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 12 2-(3-Nitro-4-chlorobenzoyl)pyridine 15.5 g. (0.153 mol) of potassium nitrate was added portionwise to a stirred solution of 33 g. (0.152 mol) of 2-(4-chlorobenzoyl)pyridine in 200 ml. of sulfuric acid, while maintaining the temperature below 40 C. After 1 hour the mixture was cautiously poured into 2 liters of ice water and neutralized with ammonium hydroxide. The resulting product 2-(3-nitro-4-chlorobenzoyl)pyridine was collected as white microneedles, mp. 98 -99 C. (cyclohexane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6318-51-0, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US4026936; (1977); A;,
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

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