Pyridine-derivatives

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

Electric Literature of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.

To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 C, was added oxalyl dichloride (16.98 mL,194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reaction mixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm) Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; HOUSE, David; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (141 pag.)WO2017/50714; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 717106-69-9, 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. 717106-69-9, name is Methyl 2-(6-chloropyridin-3-yl)acetate. A new synthetic method of this compound is introduced below.

A mixture of 0.500 g (2.69 MMOL) of Preparatory Compound A and 479 mg (2.69 MMOL) of N-BROMOSUCCINIMIDE in 5 mL of carbon TETRACHLORIDE was treated with 5 mg of azo-bis-isobutyronitrile and was heated at reflux for four hours and was allowed to cool. The mixture was concentrated to dryness and the residue was chromatographed on silica gel (230-400 mesh) using 95/5 DICHLOROMETHANE/ETHYL acetate as eluent to afford 353 mg (50%) of Preparatory Compound S methyl bromo (6-CHLORO- 3-pyridinyl) acetate as an oil ; 1HNMR (CDCI3) 6 8.44 (d, 1H, J= 2.6 HZ), 7.98 (dd, 1 H, J = 8.3 Hz and J = 2.5 Hz), 7.38 (d, 1 H, J = 8.5 Hz), 5.33 (s, 1 H), 3.82 (s, 3H); MS (ES+) m/z 265 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717106-69-9, Methyl 2-(6-chloropyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; WO2004/57960; (2004); A2;,
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 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H8ClNO

3,7-Dimethyl-1H-purine-2,6(3H,7H)-dione (300 mg, 1.67 mmol) was dissolved in N,N-dimethylformamide (10 mL), and 5-(chloromethyl)-2-methoxypyridine (263 mg, 1.67 mmol), potassium iodide (332 mg, 2.00 mmol) and potassium carbonate (461 mg, 3.34 mmol) were added. The reaction solution was heated to 120C, stirred for 3 hours and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:1 petroleum ether / ethyl acetate, Rf = 0.2) to give 1-((6-methoxypyridin-3-yl)methyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione (20.0 mg) with a yield of 4%. 1H NMR: (400 MHz, CDCl3) delta 8.28(s, 1H), 7.78(d, J = 8.0 Hz, 1H), 7.51(s, 1H), 6.67(d, J = 8.0 Hz, 1H), 5.12(s, 2H), 3.99(s, 3H), 3.91(s, 3H), 3.57(s, 3H). MS-ESI calcd. [M + H]+ 302, found 302.

With the rapid development of chemical substances, we look forward to future research findings about 101990-70-9.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Lingyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (160 pag.)EP3299371; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem