Day: June 24, 2021

Synthetic Route of 605-38-9, Adding some certain compound to certain chemical reactions, such as: 605-38-9, name is Dimethyl pyridine-2,3-dicarboxylate,molecular formula is C9H9NO4, 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 605-38-9.

Preparation of the starting substance: STR28 A solution of 19.5 g (0.1 mole) of 2,3-dimethoxycarbonyl-pyridine and 12 g (0.1 mole) of acetophenone in 300 ml of toluene is added dropwise to a suspension of 2.4 g (0.1 mole) of sodium hydride in 100 ml of toluene, while stirring. The mixture is then boiled under reflux for 3 hours, during which the methyl alcohol formed and about half of the toluene are distilled off. The residue which remains is poured onto a mixture of 15 g of ice and 7.2 g of acetic acid. The organic phase is separated off, the aqueous phase is extracted with chloroform (3 portions of 100 ml each) and the organic phases are combined, dried over sodium sulphate and evaporated in vacuo. The residue is fractionated over silica gel with chloroform as the mobile phase and chromatographed and the corresponding fractions are recrystallized from legroin. 17 g (60percent of theory) of 2-(1,3-dioxo-3-phenyl-prop-1-yl)-3-methoxycarbonyl-pyridine are obtained as white crystals of melting point 87° C.

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. 605-38-9, Dimethyl pyridine-2,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; US4752324; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 350-03-8, 1-(Pyridin-3-yl)ethanone, 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, name: 1-(Pyridin-3-yl)ethanone, blongs to pyridine-derivatives compound. name: 1-(Pyridin-3-yl)ethanone

A mixture of 30 g of 3-acetylpyridine and 60 g of N, -dimethylformamidedimethylacetal was stirred for 6 hours under reflux with heat. After cooling down to room temperature, the mixture was concentrated under reduced pressure. 3-dimethylamino-l- (pyridin-3-yl ) – propenone (43 g) was obtained. 1 H-N R (CDC13) delta: 9.09-9.07 (1H, m) , 8.68-8.65 (1H, m) , 8.19 (1H, dt), 7.85 (1H, d) , 7.38-7.34 (1H, m) , 5.68 (1H, d) , 3.19 (3H, s), 2.96 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,350-03-8, 1-(Pyridin-3-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; ARIMORI, Sadayuki; SHUTO, Akira; MIZUNO, Hajime; WO2011/49150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-99-1, 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. 13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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.

General procedure: To a solution of 2a, 2c or 2h (3 mmol, 0.5 g) in ethylene glycol (5 mL) was added successively the boronic acid (4.5 or 9.0 mmol, 1.5 or 3 equiv), Pd(PPh3)4 (1molpercent), and a solution of K3PO4 (6 mmol, 2 equiv) inwater (2 mL). The reaction mixture was heated at 80°C for 16 h and was then hydrolyzed with a 1 M solution of sodium hydroxide (20 mL). The aqueous phase was extracted with ethylacetate (3 x 30 mL) and the combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/EtOAc (60/40) as eluent.

According to the analysis of related databases, 13534-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 119285-07-3 ,Some common heterocyclic compound, 119285-07-3, molecular formula is C14H22N4O2, 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.

(5-Bromo-2-chloro-pyrimidin-4-yl) -cyclopentyl-amine (0.155 g, 0.560 mmol) and 4- (5-amino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (0.156 g9 0.560 mmol) were dissolved in toluene and heated to 115C for 48H. The reaction was cooled and concentrated. Purification on silica gel using 4: 1 HEXANE/ETOAC PROVIDED 0. 130 g (45%) OF 4- [5- (5-BROMO-4-CYCLOPENTYLAMINO- PYRIMIDIN-2-YLAMINO)-PYNIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC acid tert-butyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119285-07-3, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Formula: C5H3ClIN

Step 1 A round-bottomed flask was charged with 2-chloro-4-iodopyridine (600 mg, 2.5 mmol), thiophen-2-ylboronic acid (385 mg, 3.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (176 mg, 0.251 mmol), THF (9 mL) and 2M aqueous sodium carbonate (3.0 mL, 6.0 mmol). The reaction mixture was stirred at 70 C. overnight. The reaction mixture was cooled to room temperature then diluted with 20 mL water and extracted with 100 mL EtOAc (2*). The combined organic layers were washed with 20 mL water and 20 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on ~2 g SiO2 and chromatographed over 24 g SiO2 with EtOAc/hexanes (gradient: 0-10% EtOAc). All fractions containing product were combined and concentrated to give 430 mg (88%) of 2-chloro-4-thiophen-2-yl-pyridine as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-48-4 ,Some common heterocyclic compound, 6959-48-4, molecular formula is C6H7Cl2N, 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 suspension of calixarene 1 (0.17 g, 0.40 mmol), K2CO3(1.77 g, 12.8 mmol) and 3-(chloromethyl)pyridine hydrochloride (0.52 g, 3.2 mmol) in anhydrous CH3CN (10 ml) was stirred under nitrogen at 508C for 20 h. The reaction mixture was quenched with water and the residue was collected by filtration, dissolved in CH2Cl2 and washed withaNa2CO3 solution. The organic solvent was removed under reduced pressure and the residue was purified by column chromatography (SiO2;CH2Cl2 to CH2Cl2/ CH3OH, 95:5). The pure final product was obtained with a 51% yield (0.13 g).1H NMR (CDCl3,278C, 500 MHz): d 8.77 (s, 2H, H8),8.63 (d, J 5.0 Hz, 2H, H11), 8.06 (d, J 7.7Hz,2H, H9),7.57 (s, 2H, H6), 7.25 (dd, J1 7.7Hz, J2 5.0Hz, 2H, H10), 7.09 (d, J 7.6Hz, 4H, H4), 6.83 (d, J 7.6 Hz, 4H, H2), 6.71 (t, J 7.6 Hz, 4H, H1, H3),5.08 (s, 4H, H7), 4.26 (d, J 13.0 Hz, 4H, H5ax), 3.38 (d, J 13.0 Hz, 4H, H5eq). 13CNMR (CDCl3,278C, 125MHz): d 153.10, 151.51, 149.69, 148.78, 135.44,133.00, 132.25, 129.21, 128.58, 127.79, 125.77, 123.93, 119.25, 75.71, 31.41. ESI-MS: m/z 607 [M H], 629 [M Na]. UV- vis absorption (CH3CN, l268 nm): 1 7275M21 cm 21

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. 6959-48-4, 3-(Chloromethyl)pyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bonaccorso, Carmela; Nicoletta, Francesca; Zito, Valeria; Arena, Giuseppe; Sciotto, Domenico; Sgarlata, Carmelo; Supramolecular Chemistry; vol. 25; 9-11; (2013); p. 615 – 625;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6969-71-7, [1,2,4]Triazolo[4,3-a]pyridin-3(2H)-one, 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, Formula: C6H5N3O, blongs to pyridine-derivatives compound. Formula: C6H5N3O

At room temperature, [1,2,4] triazolo [4,3-a] pyridine-3 (2H) -one (500mg, 3.70mmol), 1,2-bromomethane (0.73mL, 8.50mmol) and DMF (10.0 mL), then NaH (125 mg) was added, and the reaction mixture was stirred at room temperature for 6 h.The reaction was quenched by adding water (30 mL), and then extracted with EA (30 mL × 2). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. Petroleum ether (10 mL) was added to it, stirred for 30 min, filtered, the filtrate was collected, and dried in vacuo to give the title compound as a red solid (490 mg, 2.02 mmol, 54.70%).

The synthetic route of 6969-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Huang Jianzhou; Ren Qingyun; Xiong Jinfeng; Liu Yang; Yu Fangcai; Liu Weishun; Wang Yifeng; Zhang Yingjun; (104 pag.)CN110903284; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64119-42-2, Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate, 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: 64119-42-2, blongs to pyridine-derivatives compound. SDS of cas: 64119-42-2

(c) ethyl 5-cyano-2-methyl-6- [4-(5-phenyl-4H-l,2,4-triazol-3-yl)piperidin-l- yl]nicotinateThe crude 4-(5-phenyl-4H- 1 ,2,4-triazolr3-yl)piperidine and ethyl 6-chloro-5-cyano-2- methylnicotinate (178 mg) were dissolved in EtOH (9 ml) and DIPEA was added. The reaction mixture was heated to 120 0C for 5 min using microwave single node heating. LCMS showed complete conversion of starting material and one by product (1,3,4- oxadiazole). NaHCO3 (aq) was added and the mixture was extracted with dichloromethane (x3). The combined organic layer was run through a phase separator and evaporated. The crude product was purified by prepHPLC [Kromasil C8, Gradient: 40 to 80 % (CH3CN/0. IM NH-iAcCXaq), pH = 7)] to afford ethyl 5-cyano-2-methyl-6-[4-(5-phenyl- 4H-l,2,4-triazot3-yl)rhoiperidin-l-yl]nicotinate. Yield 49 mg (14.8% over 3 steps). (The 1,3,4-oxadiazole was not isolated).1HNMR (500MHz, DMSOd6): 1.31 (3H, t, J=7.1Hz), 1.82-1.90 (2H, m), 2.10-2.15 (2H, m), 2.65 (3H, s), 3.15-3.26 (IH, m), 3.35-3.40 (2H, m), 4.25 (2H, q, J=7.1), 4.59-4.65 (2H, m), 7.39-7.48 (3H, m), 7.96-7.99 (2H, m), 8.34 (IH, s), 13.85 (IH, br s), MS m/z: 417 (MH-I), 415 (M-I).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64119-42-2, Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2008/4942; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15855-06-8, 2-Chloro-6-methoxypyridine-4-carboxylic 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, SDS of cas: 15855-06-8, blongs to pyridine-derivatives compound. SDS of cas: 15855-06-8

Example 4.2: (S)-2-chloro-6-methoxy-N-methyl-N-(4-M-methyl-1 H-pyrrole-2- carboxamido)-1-phenylbutan-2-yl)isonicotinamide1-Methyl-1 H-pyrrole-2-carboxylic acid ((S)-3-methylamino-4-phenyl-butyl)-amide hydrochloride (100 mg, 0.31 mmol), 2-chloro-6-methoxyisonicotinic acid (58 mg, 0.31 mmol), HOBt (74 mg, 0.466 mmol), EDC x HCI (72 mg, 0.37 mmol), and triethylamine (0.108 ml, 0.78 mmol) were dissolved in DCM (3 ml) and stirred at rt for 16 h. The mixture was concentrated and the crude product was purified by chromatography (Flashmaster, DCM to DCM:EtOAc 1 :1 over 15 min) to yield 108 mg (76 %) of the title compound as white solid. [1 H-NMR (DMSO, 600 MHz) 7.95-7.90 (m, 1 H), 7.33.7.22, 7.10-7.06 (2m, 5H), 6.87 (d, 1 H), 6.70/6.63 (d, 1H), 6.65/6.33 (s, 1 H), 6.06/5.71 (br.s, 1H), 6.00-5.97 (m, 1 H), 4.88-4.81/3.55-3.49 (m, 1H), 3.84/3.71 (s, 3H), 3.80/3.79 (s, 3H), 3.27-3.18/3.05-2.99 (m, 2H), 2.97/2.62 (s, 3H), 2.95-2.90/2.84-2.76 (m, 2H), 1.91-1.75 (m, 2H); LCMS Rtc = 2.466 min; [M+H]+ = 455.2].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15855-06-8, 2-Chloro-6-methoxypyridine-4-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; WAGNER, Juergen; ROY, Bernard, Lucien; GERSPACHER, Marc; VON MATT, Anette; BEHNKE, Dirk; WO2011/73316; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55876-84-1, 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. 55876-84-1, name is Methyl 5-(bromomethyl)picolinate. A new synthetic method of this compound is introduced below.

Example 15. Synthesis of 1-546-1. Into a 50-mL round-bottom flask, was placed methyl 5-(bromomethyl)picolinate (500 mg, 2.17 mmol, 1.00 equiv), 3-bromo-5-fluorophenol (440 mg, 2.30 mmol, 1.06 equiv), CH3CN (6 mL), and potassium carbonate (900 mg, 6.52 mmol, 3.00 equiv). The resulting solution was stirred for 60 min at 85°C. The mixture was concentrated under vacuum and the residue was diluted with 20 mL of H20. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 0.62 g (77percent) of methyl 5-((3-bromo-5- fluorophenoxy)methyl)picolinate as a yellow solid.LC-MS: ( +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55876-84-1, its application will become more common.

Reference:
Patent; MERIAL LIMITED; MENG, Charles, Q.; MURRAY, Clare, Louise; BLUHN-CHERTUDI, Itta; SOUKRI, Mustapha; WO2013/3505; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem