Tag: M.W:100-200

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

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

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 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

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

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

Synthetic Route of 17282-00-7 , The common heterocyclic compound, 17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine, molecular formula is C6H7BrN2, 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: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 17282-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
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 56700-70-0, name is tert-Butyl pyridin-3-ylcarbamate. This compound has unique chemical properties. The synthetic route is as follows. Safety of tert-Butyl pyridin-3-ylcarbamate

In heat-dried argon purged 4-neck flask was placed a solution of pyridin-3-yl-carbamic acid tert-butyl ester (10 g, 51.5 mmol, CAS RN 56700-70-0) in THF (100 mL). After cooling down to -75 C., tert-butyllithium (1.7M solution in n-pentane, 66.6 mL, 113 mmol) was added dropwise over 15 min keeping the temperature below -60 C. The resulting light brown suspension was stirred at -75 C. for 3.75 h. A solution of iodine (28.7 g, 113 mmol) in THF (50 mL) was added dropwise over 20 min. below -63 C. The reaction mixture was stirred at -75 C. for 1.5 h and then poured on saturated aqueous NH4Cl solution (1000 mL) and EtOAc (500 mL). The layers were separated. The organic layer was washed once with 10% aqueous Na2S2O3 solution (300 mL) and once with brine (250 mL), dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 120 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Yellow solid (11.7 g; 71%). MS (ESI): m/z=321.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 56700-70-0.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Karnachi, Prabha Saba; Kim, Kyungjin; Martin, Rainer E.; Mattei, Patrizio; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ullmer, Christoph; US2012/232051; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1990-90-5 , The common heterocyclic compound, 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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 total of 20.628 mg (0.1 mmol) of S-IBU and 10.814mg (0.1 mmol) of 3M4AP were dissolved in methanol-H2O (3:1, v: v) and left for slow evaporation at ambient conditions. Good quality single crystals were obtained for SCXRD after 10 days

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Dejia; Pei, Tiezhu; Bai, Yunhe; Zhou, Lina; Bao, Ying; Yin, Qiuxiang; Xie, Chuang; Journal of Molecular Structure; vol. 1179; (2019); p. 487 – 494;,
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 16063-69-7, name is 2,4,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2Cl3N

EXAMPLE 12-1Preparation of Compound 12-L [0672j A solution of 2,4,6-trichioropyridine (6.5 g, 36 mmol) in anhydrous methanol (20 mL) was added MeONa (2.9 g, 54 mmol) at 0C. The reacton mixture was stirred at rt for 12 h. The reaction was quenched with dry ice, and the mixture was filtered. The solution was concentrated under reduced pressure, and the residue was dissolved in EA. The mixture was washed with water, and the organic layers were dried over NaSO4. The solvent was concentrated to give 12-L (4.2 g, 67%).

With the rapid development of chemical substances, we look forward to future research findings about 16063-69-7.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; WO2014/31784; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem