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. 884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

2-Fluoro-5-morpholinopyridin-3-amine A stirred mixture of 3-amino-5-bromo-2-fluoropyridine (0.96 g, 5.02 mmol), L-proline (0.12 g, 1.01 mmol), potassium carbonate (1.39 g, 10.1 mmol), copper(I) iodide (0.096 g, 0.50 mmol), and morpholine (1.31 mL, 15.04 mmol) in dry DMSO (3.0 mL) was purged three times with argon and placed under vacuum three times, then the mixture was heated to 90 C. After 21.5 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organics were combined and dried over anhydrous sodium sulfate. After filtration and concentration the residue was purified on basic alumina (10-50% EtOAc in hexanes) to afford a white solid as 2-fluoro-5-morpholinopyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.96 (1H, t, J=2.6 Hz), 6.75 (1H, dd, J=9.6, 2.7 Hz), 5.25 (2H, br. s.), 3.80 (4H, m), 3.08 (4H, m). Mass Spectrum ESI (pos.) m/e: 198.1 (M+H)+.

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, 884495-22-1, 5-Bromo-2-fluoropyridin-3-amine.

Reference:
Patent; AMGEN INC.; US2010/331293; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 85148-26-1, 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 85148-26-1, name is 3-Chloro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Under an N2atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol%),dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol)were successively added into a Schlenk tube. The mixture wasstirred vigorously at 90C for 4 h. Then the solvent was removedunder reduced pressure and the residue was purified by columnchromatography on silica gel (eluent:PE/EA = 15:1) to give the pureproducts. The reported yields are the average of two runs.The catalytic reactions have been given in Tables 4-7. The result-ing amines were identified by comparison of the1H and13C NMRdata with those previously reported (ESI).

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 85148-26-1, 3-Chloro-5-(trifluoromethyl)pyridine.

Reference:
Article; Nirmala, Muthukumaran; Prakash, Govindan; Ramachandran, Rangasamy; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 56 – 67;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67346-74-1 ,Some common heterocyclic compound, 67346-74-1, molecular formula is C7H6N2, 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.

To a tetrahydrofuran (3 mL) solution of (4-butyl-phenyl)-acetohydroximoyl chloride (150 mg, 0.665 mmol) described in Manufacturing Example 70-1-3 and 3-ethynyl-pyridin-2-ylamine (50 mg, 0.424 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (232 muL, 1.66 mmol) at room temperature, which was stirred for 8 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (55 mg, 18percent). 1H-NMR Spectrum (CDCl3) delta (ppm): 0.91-0.94 (3H, m), 1.31-1.40 (2H, m), 1.55-1.63 (2H, m), 2.57-2.61 (2H, m), 4.03 (2H, s), 5.53 (2H, brs), 6.26 (1H, s), 6.70-6.73 (1H, m), 7.14-7.20 (4H, m), 7.71-7.73 (1H, m), 8.11-8.13 (1H, m).

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. 67346-74-1, 3-Ethynylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); 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. 945954-95-0, name is 6-Bromo-3-methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H6BrNO2

To a solution of 6-bromo-3-methoxypicolinaldehyde (0.13 g, 0.60 mmol) in THF (6 mL) and tBuOH (6 mL) was added 2-methyl-2-butene (0.64 mL, 2.41 mmol), followed by an aqueous solution (2 mL) of sodium dihydrogen phosphate (0.29 mg, 2.4 mmol) and NaC102 (0.22 mg, 2.4 mol). The resulting mixture was stirred at RT for 16 hrs. The volatiles were then evaporated in vacuo and the residue thus obtained was purified on silica gel eluting with a solvent gradient of 0 to 10% MeOH in DCM (with 2% acetic acid as an additive in DCM) to afford 6-bromo-3-methoxypicolinic acid as a solid.

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, 945954-95-0, 6-Bromo-3-methoxypicolinaldehyde.

Reference:
Patent; INCEPTION 2, INC.; STOCK, Nicholas, Simon; CHEN, Austin, Chih-Yu; BRAVO, Yalda, Mostofi; JACINTHO, Jason, Duarte; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; CLARK, Ryan, Christopher; TRUONG, Yen, Pham; WO2013/134562; (2013); 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. 76006-13-8, name is 3-Bromo-1H-pyrazolo[3,4-c]pyridine, the common compound, a new synthetic route is introduced below. Safety of 3-Bromo-1H-pyrazolo[3,4-c]pyridine

ii) Preparation of 3-bromo-1-(2-chloro-6-(trifluoromethyl)benzyl)-1H-pyrazolo[4,3-b]pyridine (A-4) A mixture of 2-chloro-6-(trifluoromethyl)benzyl 4-methylbenzenesulfonate (A-2) (0.19 g, 0.51 mmol), 3-bromo-1H-pyrazolo[3,4-c]pyridine (A-3) (0.1 g, 0.51 mmol), t-BuOK (0.11 g, 1.02 mmol) and TBAI (75 mg, 0.20 mmol) in THF (5 ml) was heated at 60 C. for 14 h. The reaction mixture was cooled down, diluted with saturated NH4Cl solution (20 ml) and extracted with ethyl acetate (30 ml*2). The combined organic layers were washed with brine (20 ml), dried over anhydrous Na2SO4 and concentrated to give the title compound A-4 as a brown oil. LCMS (ESI) calc’d for C14H8BrClF3N3 [M+H]+: 390. found: 390.

The synthetic route of 76006-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barr, Kenneth J.; Bienstock, Corey E.; MacLean, John K.; Zhang, Hongjun; Beresis, Richard T.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/210687; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-10-8, 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 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure B: To a 5 mL vial back-filled with dried air,compound 1 (1.0 equiv., 0.2 mmol), benzyl bromides (6.0 equiv., 1.2 mmol), and Na2CO3 (2.0 equiv. 0.4 mmol, 42 mg) in sulfolane (0.5 mL) were added, and the reaction was heated at 90 C for 18 h. Upon the completion of the starting materials, the reaction mixture was dissolved in 100 mL H2O, and extracted with dichloromethane (40 mL 3). The organic layers were combined, dried over anhydrous Na2SO4, and removed. The crude was purified by using silica gel column chromatography (PE/EA 10:1e1:2 as eluents) to afford the target compound 2.

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 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine.

Reference:
Article; Xu, Huayan; Xu, Liang; Luo, Xiaowei; Wang, Junfeng; Zhou, Xuefeng; Yang, Bin; Li, Ding; Luo, Zaigang; Liu, Yonghong; Liao, Shengrong; Tetrahedron; vol. 75; 19; (2019); p. 2785 – 2796;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, 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, SDS of cas: 175205-82-0, blongs to pyridine-derivatives compound. SDS of cas: 175205-82-0

Step 2. Synthesis of methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate In a 500 mL round-bottom flask equipped with a magnetic stirrer and argon inlet, methyl 3-amino-6-(trimethylstannyl)pyrazine-2-carboxylate (20.92 g, 55.0 mmol), 2-Bromo-3- (trifluoromethyl) pyridine (14.38 g, 60.5 mmol), Pd2(dba)3 (5.54 g, 6.05 mmol) and P(o-Tol)3 (3.79 g, 12.09 mmol) were dissolved in DMF (100 ml) at rt, followed by addition of NEt3 (10.72 ml, 77 mmol). The reaction mixture was heated to 110C under argon for 1 h. After cooling to rt, the reaction mixture was filtered through celite, washed with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using ethyl acetate heptane which gave methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate (7.8 g) as a yellow solid. LC-MS (Basic Method ): ret.time= 0.93 min, M+H = 299.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 171178-45-3, 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 171178-45-3 as follows.

EXAMPLE 181-(((5S JS)-3-(6-Chloropyridin-3-yl)-7-methyl-2-oxo-1-oxa-3-azaspiror4.5ldecan-7-yl)methyl)-1 H-benzordlimidazole-6-carbonitrileA 5 ml. microwave vial was charged with 1-(((3S,5S)-5-methyl-1-oxaspiro[2.5]octan-5- yl)methyl)-1 H-benzo[d]imidazole-6-carbonitrile (200 mg, 0.711 mmol), tert-butyl (6-chloropyridin- 3-yl)carbamate (195 mg, 0.853 mmol), potassium tert-butoxide (96 mg, 0.853 mmol) and DMF. The tube was sealed and heated to 70 C for 16 h. The reaction mixture was loaded onto a 10 g SCX SPE and eluted with 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH. The ammonia fractions were combined and concentrated and the crude product then purified by Waters reverse phase HPLC (20% to 60% MeCN, 0.1 %TFA, 16 min, 50 mL/min, Sunfire column) to afford the TFA salt of 1-(((5S,7S)-3-(6-chloropyridin-3-yl)-7-methyl-2-oxo-1- oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1 H-benzo[d]imidazole-6-carbonitrile as a cream solid (55 mg, 12.67 % yield). MS (m/z) 435.9 (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,171178-45-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 845827-15-8, Adding some certain compound to certain chemical reactions, such as: 845827-15-8, name is Methyl [2,3′-bipyridine]-6′-carboxylate,molecular formula is C12H10N2O2, 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 845827-15-8.

2,3′-Dipyridine-6′-carboxylic acid (1) Conducting the operations similar to those of Production Example 14 using 2-iodopyridine and 6-bromo-3-pyridineboronic acid, 6′-bromo-2,3′-dipyridine was obtained. (2) The compound (330 mg) as obtained in above (1), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium and triethylamine (0.7 ml) were added to a DMF-methanol mixed solution (DMF/methanol; 5/1 ml) and stirred in carbon monoxide atmosphere at 80C for a day and night, to provide methyl-2,3′- dipyridine-6′-carboxylate (160 mg). Hydrolyzing this with 5N aqueous sodium hydroxide solution, the title compound (110 mg) was obtained as white solid. ESI-MS Found:m/z 201 [M+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. 845827-15-8, Methyl [2,3′-bipyridine]-6′-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1657242; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14432-12-3, 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 14432-12-3, name is 4-Amino-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-amino-2-chloropyridine (193 mg, 1.50 mmol), di-tert-butyl-di- carbonate (393 mg, 1.80 mmol) and 4-dimethylaminopyridine (1.8 mg, 0.02 mmol) in acetonitrile (5 mL) was stirred at room temperature for 18 hours. This mixture was concentrated under reduced pressure. The residue was purified by column chroma- tography on silica-gel (hexane/ethyl acetate, 20: 1) to give tert-butyl (2-chloropyridin- 4-YL) carbamate (250 mg, 73%).

According to the analysis of related databases, 14432-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/43926; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem