Month: June 2021

Synthetic Route of 19755-53-4, 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. 19755-53-4, name is 2-Bromo-3-nitropyridine. A new synthetic method of this compound is introduced below.

2. N-(4-TERT-BUTYL-PHENYL)-4- (3-NITRO-PYRIDIN-2-YL)-BERAZAMIDE Bubble nitrogen through a solution of 4-BORONO-N- (4-TERT-BUTYL-PHENYL)-BENZAMIDE (1.3 g, 4.37 mmol), 2-bromo-3-nitro-pyridine (0. 63 g, 3.12 mmol), 2M NA2CO3 (3.9 ml, 2.5 equivalents), in DME for 10 minutes. Add Pd (PPH3) 4 (144 mg) and bubble nitrogen through the solution for two additional minutes. Heat the reaction for 12 hours at 80C. Cool the reaction, concentrate, and partition between EtOAc and water. Dry the solution (Na2SO4) and concentrate under reduced pressure to give the crude product. Purify using chromatography (25% ethyl acetate/hexanes eluent) to give N- (4-tert-butyl-phenyl)-4- (3- nitro-pyridin-2-yl)-benzamide as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19755-53-4, 2-Bromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/56774; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1597-32-6, 2-Amino-6-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, SDS of cas: 1597-32-6, blongs to pyridine-derivatives compound. SDS of cas: 1597-32-6

To a solution of 6-fluoropyridin-2-amine (1.12 g, 10 mmol) in DMF (16 mL) was added NaH (0.24 g, 60% dispersion in mineral oil, 10 mmol) and the mixture stirred for 0.5 h. To the mixture was added 6-chloro-N-(6-fluoropyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.93 g, 4 mmol) under N2. The mixture was stirred at room temperature for 16 h, then partitioned between 45 mL of saturated NH4Cl solution and 45 mL of ether. The organic layer was washed with water (30 mL×3) and saturated NaCl solution (30 mL×3), dried over Na2SO4, concentrated in vacuo, and purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-N-(6-fluoropyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (1.04 g, 99%) as a light brown solid. LC-MS: [M+H]+, 264.1, 266.2, tR=1.601 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1597-32-6, 2-Amino-6-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (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. 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-5-chloropyridin-2-amine

Step 2: tert-Butyl 4-(6-(6-amino-3-chloropyridin-2-yl)-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate A mixture of tert-butyl 4-(5-chloro-7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c]isothiazol-3-yl)piperazine-1-carboxylate (99.5 mg, 0.200 mmol), SPhos Pd G3 (17.3 mg, 0.020 mmol), 6-bromo-5-chloropyridin-2-amine (Combi-blocks Inc., San Diego, Calif., USA, 124 mg, 0.6 mmol), sodium carbonate (85 mg, 0.80 mmol) in water (0.25 mL), and 1,2-DCE (0.75 mL) was heated at 50 C. for 2 h. The reaction mixture was concentrated in vacuo and chromatographically purified (silica gel, 0% to 100% (3:1) EtOAc-EtOH in heptane) to give tert-butyl 4-(6-(6-amino-3-chloropyridin-2-yl)-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate: m/z (ESI, +ve) 498.0 (M+H)+.

The synthetic route of 1004294-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]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, 866546-07-8, blongs to pyridine-derivatives compound. Safety of 5-Chloro-1H-pyrrolo[2,3-b]pyridine

General procedure: In a microwave reaction vial with a magnetic stirring bar was placed the azaindoleor indole (0.38 mmol), aldehyde (0.19 mmol), and K2CO3 (176 mg, 1.27 mmol), followedby addition of 2.5 mL of 1:1 mixture of MeOH:H2O. The resulting mixture was placed ina microwave reactor and irradiated at 130 oC for 30 minutes. After cooling to roomtemperature, the volatiles were removed under reduced pressure. The crude residue wasdiluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combinedorganic layers were dried over sodium sulfate, filtered, and the resulting filtrate evaporated in vacuo to give a crude solid that was purified using reversed-phase HPLC,eluting with MeCN/H2O with a trace of TFA to give the desired compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,866546-07-8, its application will become more common.

Reference:
Article; Uddin, Md. Imam; Buck, Jason R.; Schulte, Michael L.; Tang, Dewei; Saleh, Samir A.; Cheung, Yiu-Yin; Harp, Joel; Manning, H. Charles; Tetrahedron Letters; vol. 55; 1; (2014); p. 169 – 173;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55758-32-2, 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 55758-32-2 as follows.

Preparation of 2-fluoro-5-[3-(tetrahydro-2H-pyran-2-yloxy)bropoxy]byridine Bromoacetaldehyde diethyl acetal (2.29 ml, 13.3 mmol) and cesium carbonate (10.08 g, 30.9 mmol) were added to an N,N-dimethylacetamide solution (20 ml) of 6-fluoropyridin-3-ol (1 g, 8.84 mmol), and stirred under a nitrogen atmosphere at 100C for 6 hours. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 7:1 1 to 3:1) to obtain a colorless oil (2.47 g) containing 2-fluoro-5-[3-(tetrahydro-2H-pyran-2-yloxy)propoxy]pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55758-32-2, its application will become more common.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2221301; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63897-12-1, 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. 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, 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.

EXAMPLE 238 3-Amino-2,4-bis(methylthio)-6-methylpyridine To a solution of 15.5 g (0.22 mol) sodium methanethiolate in 200 ml methanol was added slowly with stirring under nitrogen a solution of 20.8 g (0.1 mol) 3-nitro-2,4-dichloro-6-methylpyridine in 150 ml methanol. A precipitate formed and the mixture was stirred overnight at room temperature. The mixture was then filtered and the solid was washed first with methanol and then with water. 3-Nitro-2,4-bis(methylthio)-6-methylpyridine (18.9 g, 82% yield) was obtained as a yellow solid, mp 172-176 C. 1 H NMR (CDCl3): delta 2.45 (s, 3H); 2.51 (s, 3H); 2.55 (s, 3H); 6.77 (s, 1H).

According to the analysis of related databases, 63897-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5362878; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 61338-13-4, 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic 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, 61338-13-4, blongs to pyridine-derivatives compound. Safety of 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic acid

To a 1000 ml three-necked flask, 600 ml of tetrahydrofuran, 2- (4-methyl-2-phenyl-1-piperazinyl)(134 g, 0.45 mol),Zinc chloride (306 g, 2.25 mol) was added sodium borohydride (85 g, 2.25 mol) in portions carefully. The temperature was raised to 60-85 C after addition and reflux with stirring for 16 hours, cooled to 0 C and carefully quenched with methanol The reaction mixture was removed under reduced pressure. 600 ml of 6N hydrochloric acid was added and the mixture was heated to 80 C with heating and stirred for 1 hour. The mixture was cooled to room temperature and extracted with methylene chloride (2 L × 3). The organic phase was dried over 1 kg of anhydrous sodium sulfate, A white solid was obtained. The white solid was further dried by blowing with air at 50 C to give 113 g of 1-(3-hydroxymethylpyridin-2-yl) -4-methyl-2-phenylpiperazine as a white solid in 89% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61338-13-4, its application will become more common.

Reference:
Patent; Beijing Ha Sanlian Science And Technology Co., Ltd.; Harbin Sanlian Pharmaceutical Co., Ltd.; Liu Jinai; Li Yuanzhen; Ning Ruibo; Wang Mingxin; (8 pag.)CN105367571; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 84539-30-0, 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.84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.

To a microwave reaction vial was added N-(5-fert- butylisoxazol-3-yl)-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)acetamide from Step 1 of Example 85 (350 mg, 0.91 mmol), 5-bromo-N- methylpyridin-2-amine (256 mg, 1.37 mmol), 2M aq sodium carbonate (1.37 mL, 2.73 mmol), acetonitrile (10 mL), and [1,1′- bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (74.3 mg, 0.091 mmol). The vial was purged with argon, sealed, and heated in a microwave reactor at 150 C for 15 min. The mixture was partitioned between EtOAc (50 mL) and water (50 mL), and the aqueous layer was separated and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine (2 ^ 30 mL), dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with 0 – 70% EtOAc in hexanes to give N-(5-tert-butylisoxazol-3-yl)-2-(4-(6-(methylamino)pyridin-3- yl)phenyl)acetamide (165 mg, 50%) as an off-white solid. 1H NMR (300 MHz, DMSO-t/6) 6 11.20 (s, 1H), 8.30 (d, J= 2.3 Hz, 1H), 7.69 (dd, J= 2.4, 8.7 Hz, 1H), 7.52 (d, J= 8.1 Hz, 2H), 7.34 (d, J= 8.3 Hz, 2H), 6.61 (d, J= 4.7 Hz, 1H), 6.57 (s, 1H), 6.52 (d, J= 8.7 Hz, 1H), 3.66 (s, 2H), 2.80 (d, J= 4.9 Hz, 3H), 1.27 (s, 9H). LC- MS (ESI) m/z 365 (M +H)+.

Statistics shows that 84539-30-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-N-methylpyridin-2-amine.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 55676-22-7, name is 3-Acetyl-6-chloropyridine, molecular formula is C7H6ClNO, 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. name: 3-Acetyl-6-chloropyridine

To a solution of 1-(6-chloropyridin-3-yl)ethanone (4.0 gm, 0.0257 mole) in DMF (15 mL), cesium carbonate (16.8 gm, 0.051 mole) was added followed by addition of methyl 2-hydroxyacetate (8.0 ml, 0.103 mmoles) at 25 C under nitrogen atmosphere and the reaction mixture was stirred at 80-90 C for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure. The crude product was purified by colunm chromatography (Eluent: 16% ethyl acetate in hexane) to yield 1.25 gm (23%) of product as off white solid. 1H NMR: DMSO-d6, delta2.55 (s, 3H), 3.67 (s, 3H), 5.02 (s, 2H), 7.04 (dd, J = 8.8 & 0.4 Hz, 1H), 8.20 (dd, J = 8.8 & 2.4 Hz, 1H), 8.78 (d, J = 2.0 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 55676-22-7.

Reference:
Patent; Cadila Healthcare Limited; PINGALI, Harikishore; MAKADIA, Pankaj; PANDYA, Vrajesh; KALAPATAPU, V. V. M. Sairam; JAIN, Mukul R.; EP2658851; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76196-79-7, 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. 76196-79-7, name is Ethyl 6-cyanonicotinate. A new synthetic method of this compound is introduced below.

[0148] To a solution of ethyl 6-cyano-3-pyridinecarboxylate (3.75 g) and cone. HCl (7.5 mL) in 225 mL ethanol was added 10% Pd/C (wet, 375 mg) and the reaction mixture was hydrogenated using hydrogen balloon and stirred for 12 h. Solution was filtered through celite and ethanol was evaporated to give ethyl 6-(aminomethyl)-3-pyridinecarboxylate HCl as a white solid, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76196-79-7, Ethyl 6-cyanonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102142; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem