Day: August 30, 2021

Adding a certain compound to certain chemical reactions, such as: 55589-47-4, 3-Methylpicolinaldehyde, 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: 3-Methylpicolinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 3-Methylpicolinaldehyde

(7-(4-Methylpiperazin-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl)methanamine (50 mg, 0.2 mmol) was dissolved in 2 mL of DCE (1,2-Di Chloroethane) 3-methyl-2-pyridinecarboxaldehyde (0.2 mmol, 24 mg) and NaBH(OAc)3 (64 mg, 0.3 mmol) were added and the mixture was stirred at room temperature for 2 h. Diluted with DCM and washed with saturated sodium bicarbonate and saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated by filtration, and the residue was purified by column chromatography to give the title compound as a pale yellow gum (46percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55589-47-4, 3-Methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Cao Bin; (103 pag.)CN103570683; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1264193-11-4 ,Some common heterocyclic compound, 1264193-11-4, molecular formula is C7H5BrN2, 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.

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

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. 1264193-11-4, 6-Bromopyrazolo[1,5-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 127406-56-8, Adding some certain compound to certain chemical reactions, such as: 127406-56-8, name is 4-Pyridin-2-yl-benzaldehyde,molecular formula is C12H9NO, 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 127406-56-8.

EXAMPLE 13; Synthesis of 3,5-dichloro-4-(pyridine-2-yl)benzaldehyde (5b)In a 40 mL tube, 4-(pyridine-2-yl)benzaldehyde (0.3 mmol, 1 equiv) and CuCl2 (8.1 mg, 0.06 mmol, 20% equiv) were dissolved in 1 mL of CI2CHCHCI2 under oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 24 h. The reaction mixture was diluted with 20 mL of CH2CI2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.12 in 2:1 hexane: ether), the title product was obtained as a white solid (62.0 mg, 82%).1H NMR (400 MHz, CDCl3) delta 9.99 (s, IH), 8.78 (d, J= 4.8 Hz, IH), 7.92 (s, 2H), 7.86 (td, J= 8.0, 1.2 Hz, IH), 7.41-7.39 (m, H), 7.35 (d, J= 8.0 Hz, IH); 13C NMR (100 MHz, CDCl3) delta 189.60, 154.86, 150.23, 143.90, 137.66, 136.98, 136.34, 129.27, 124.98, 123.82; IR (thin film) v 3067, 1706, 1549, 1364, 1200 cm” ‘; HRMS (TOF) Calcd for Ci2H8Cl2NO (M + H) 258.0452, found 258.0456.

According to the analysis of related databases, 127406-56-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRANDEIS UNIVERSITY; WO2007/123910; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 128071-75-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.128071-75-0, name is 2-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.

General procedure: A mixture of the appropriate o-haloaldehyde (1 eq, 2.60mmol), methyl propargyl ether (1.2 eq, 3.12mmol), Pd(PPh3)2Cl2 (0.04 eq, 0.10mmol), CuI (0.075 eq, 0.19mmol), Et3N (1.5 eq, 3.90mmol), in dry DMF (12mL), was stirred under nitrogen atmosphere, at room temperature for 1h. The mixture was quenched with H2O and the product was extracted with Et2O. The combined organic layers were washed with water, brine, dried over Na2SO4, and evaporated. The crude product was purified by FC (petroleum ether/AcOEt 6:4).

Statistics shows that 128071-75-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromonicotinaldehyde.

Reference:
Article; Dore, Antonio; Asproni, Battistina; Scampuddu, Alessia; Pinna, Gerard Aime; Christoffersen, Claus Tornby; Langgard, Morten; Kehler, Jan; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 181 – 193;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3510-66-5, 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. 3510-66-5, name is 2-Bromo-5-methylpyridine, molecular formula is C6H6BrN, 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.

36 g (209 mmol) 2-Bromo-5-methylpyridine and 37.5 g(418 mmol) copper cyanide are refluxed for two hours in 500 mldimethylformamide. After cooling down to50 C, 10percent aqueous ammonia solution (500 ml) is added with stirring. The product is extracted with dichloromethane, the organic phase is dried over magnesium sulfate, and the solvent is removed invacuo. The product is purified by column chromatgraphy (silica, eluent cyclohexane/ethyl acetate 9: 1). Yield: 18 g (73percentof th.)IH-NMR (300MHz, CDCIs) :8 = 2.4 (s, 3H); 7.6(m, 2H); 8.6 (s,1H) ppm.

According to the analysis of related databases, 3510-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20410; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16665-38-6, (4-Methoxypyridin-2-yl)methanol, 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, 16665-38-6, blongs to pyridine-derivatives compound. Formula: C7H9NO2

14. 2-Chloromethyl-4-methoxypyridine hydrochloride 15 ml of thionyl chloride are added dropwise to a solution, cooled to -10 C., of 10 g (0.072 mole) of 2-hydroxymethyl-4-methoxypyridine in 30 ml of dry chloroform in the course of 15 minutes. The solution is allowed to come to room temperature and stirring is continued for one and a half hours. After the solvent and the excess thionyl chloride have been stripped off, colorless crystals are obtained, and these are recrystallized from isopropanol [12.1 g (87%), m.p. 149-150 C., decomposition].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16665-38-6, its application will become more common.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US4560693; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944401-77-8, 2-Amino-4-fluoropyridine, 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 2-Amino-4-fluoropyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Amino-4-fluoropyridine

In an aluminium foil-covered flask, Intermediate 51 (62.3 g, 506 mmol) was dissolved in acetonitrile (1500 mL), and NBS (86 g, 481 mmol) was added. The mixturewas stirred at ambient temperature for 2 h. The mixture was concentrated to afford a yellow solid. The crude material was dissolved in EtOAc (1000 mL), washed twice with saturated aqueous sodium bicarbonate solution, then with brine, dried with sodium sulphate, filtered and concentrated in vacuo, to afford a light brown solid (71.2 g). The crude material was crystallized from EtOAc (300 mL) and heptane (300 mL) to give the title compound (34.3 g) as brown crystals. LCMS 191(79Br)/193(81Br) [M+H], RT 0.79 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944401-77-8, 2-Amino-4-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); 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. 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-5-nitropyridine

Example BPreparation of 3-bromo-2-cyclopropylmethoxy-5-nitro-pyridineTo a solution of sodium hydride (2.21 g, 55.34 mmol) in anhydrous DMF (20ml) was added cyclopropylmethanol (CAS Registry No. 2516-33-8) (12.45 ml, 153.2 mmol) under nitrogen at 0 C and the reaction mixture was stirred at 25 C for 30 minutes. Then 3-bromo-2- chloro-5-nitropyridine (CAS Registry No. 5470-17-7) (7.3 g, 30.74 mmol) was added drop wise at 0 C and stirred for two hours at 25 C. Water (60ml) was added to the reaction mixture and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water and brine, dried over Na2S04 and evaporated under reduced pressure to get the crude residue (12 g). The crude was purified by column chromatography (2% ethyl acetate/hexane) to get the desired product (2.06 g, 32%) as light yellow solid and 1.7g of unreacted 3-bromo-2-chloro-5- nitropyridine was recovered. MS (LC/MS): not responding, NMR is in agreement with the structure: 1H-NMR (400 MHz, CDC13): delta 0.41 (m, 2H), 0.65 (m, 2H), 1.32 (m, 1H), 4.34 (d, 2H), 8.60 (d, 1H), 8.96 (d, 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, 5470-17-7, 3-Bromo-2-chloro-5-nitropyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GRETHER, Uwe; HEBEISEN, Paul; HOFFMANN, Torsten; ROEVER, Stephan; WO2012/49190; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73290-22-9, Adding some certain compound to certain chemical reactions, such as: 73290-22-9, name is 2-Bromo-5-iodopyridine,molecular formula is C5H3BrIN, 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 73290-22-9.

Step 1: 2-Bromo-5-trimethylsilanylethynyl-pyridine 2-Bromo-5-iodopyridine (2.5 g, 8.8 mmol) was dissolved under nitrogen in 50 ml THF. Bis-(triphenylphosphine)-palladium(II) dichloride (618 mg, 880 mumol, 0.1 equiv.), ethynyltrimethylsilane (950 mg, 1.34 ml, 9.6 mmol, 1.1 equiv.), triethylamine (1.78 g, 2.44 ml, 17.6 mmol, 3 equiv.) and copper(I) iodide (84 mg, 440 mumol, 0.05 equiv.) were added and the mixture was stirred for 3 hours at 50 C. The reaction mixture was cooled and evaporated to dryness. The crude product was purified by flash chromatography on silica gel, eluting with an ethyl acetate:heptane gradient 0:100 to 15:85. The desired 2-bromo-5-trimethylsilanylethynyl-pyridine (1.95 g, 7.7 mmol, 87% yield) was obtained as a white solid, MS: m/e=254.1/256.1 (M+H+).

According to the analysis of related databases, 73290-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 91182-50-2, Adding some certain compound to certain chemical reactions, such as: 91182-50-2, name is 3-Bromo-2-phenylpyridine,molecular formula is C11H8BrN, 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 91182-50-2.

Molecules 1 (2 mmol, 466 mg) and iridium trichloride trihydrate (1 mmol, 352 mg) were weighed into a round-bottomed flask, evacuated, and bubbling nitrogen, and circulated three times. Under a nitrogen atmosphere, 16 mL of a mixed solution of ethylene glycol ether and water (3: 1, v / v) was injected and dissolved by stirring. After reacting at 110 C for 24 hours, the crude product was cooled to room temperature, and filtered through a sand core funnel to obtain a solid, which was washed three times with deionized water and ethanol. The product is obtained after drying in a vacuum drying box.

According to the analysis of related databases, 91182-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Zhang Yin; Wang Jun; Lan Yiping; Zhao Qiang; Liu Shujuan; Huang Wei; (11 pag.)CN110330532; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem