Day: August 16, 2021

Synthetic Route of 1013648-04-8, Adding some certain compound to certain chemical reactions, such as: 1013648-04-8, name is Methyl 2,6-dichloro-4-methylnicotinate,molecular formula is C8H7Cl2NO2, 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 1013648-04-8.

) Synthesis of 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterA solution of 5.2 g (23.7 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester, 3.94 g (28.5 mmol) K2C03 and 2.06 ml (23.7 mmol) morpholine in DMF (48 ml) was heated to 60 C for 16 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1 ) provided 1.95 g (7.2 mmol, 30%) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

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. 1013648-04-8, Methyl 2,6-dichloro-4-methylnicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887583-90-6, 4-Bromo-2-(trifluoromethyl)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, COA of Formula: C6H3BrF3N, blongs to pyridine-derivatives compound. COA of Formula: C6H3BrF3N

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 10.6 mL, 13.8 mmol) was added dropwise by syringe to a solution of 4-bromo-2-(trifluoromethyl)pyridine (3.12 g, 13.8 mmol) in dry THF (50 mL) at 0 C. After 30 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.38 g, 12.5 mmol) in THF (28.5 mL) was added to the Grignard solution by syringe at 0 C. The reaction mixture was warmed to room temperature over 2 hours after which it was quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887583-90-6, 4-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6271-78-9 ,Some common heterocyclic compound, 6271-78-9, molecular formula is C6H5ClN2O, 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.

Example 1-6 6-chloro-N-(7-chloro-2-(oxazol-2-yl)-4-oxo-1-phenyl-1,4-dihydroquinolin-3-ylmethyl)nicotin-amide A 5 mL round-bottomed flask was charged with 6-chloronicotinamide (14 mg, 0.091 mmol), sodium hydride (60% suspension in mineral oil, 5.0 mg, 0.013 mmol) and DMF (1 mL) to give a slightly white suspension. This mixture was stirred at 50 C for 15 min. During this time, the reaction mixture became more cloudy and difficult to stir. The reaction mixture was cooled to room temperature. A solution of 3-(bromomethyl)-7- chloro-2-(oxazol-2-yl)-l-phenylquinolin-4(lH)-one (38 mg, 0.091 mmol) in DMF (1 mL) was added dropwise to the room temperature reaction mixture. The reaction was stirred at 50 C over 1 hr. LC/MS at this time suggested formation of the desired product. The reaction mixture was allowed to cool gradually to room temperature, then it was stirred at room temperature overnight. The reaction was quenched via addition of 1 mL water slowly. The quenched reaction mixture was then partitioned between 20 mL ethyl acetate and 20 mL water. The organic phase was dried (MgS04), filtered, then concentrated over silica gel. The silica gel supported crude product was loaded onto a 40 gram silica gel column. Flash chromatography (75% ethyl acetate-hexanes ramped to 100% ethyl acetate) was used to partially purify the desired product 6-chloro-N-(7-chloro-2-(oxazol- 2-yl)-4-oxo- 1 -phenyl- 1 ,4-dihydroquinolin-3-ylmethyl)nicotinamide from the side product 6-chloro-N,N-bis((7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3- yl)methyl)nicotinamide. Homogeneous fractions were concentrated to provide 6-chloro- N-(7-chloro-2-(oxazol-2-yl)-4-oxo-l -phenyl- l,4-dihydroquinolin-3-ylmethyl)nicotin- amide as 1 mg (2% yield) of a white solid. 1H NMR (chloroform-d) delta ppm 8.75 (d, 7=2.4 Hz, 1 H) 8.42 (d, 7=8.6 Hz, 1 H) 7.99 (dd, 7=8.2, 2.7 Hz, 1 H) 7.68 (bs, 1 H), 7.58 (s, 1 H), 7.45 (m, 3 H), 7.39 (dd, 7=8.5, 2.0 Hz, 1 H) 7.34 (d, 7=8.2 Hz, 1 H) 7.28 (m, 2H) 7.13 (s, 1H) 6.85 (d, J=2.0 Hz, 1 H) 4.47 (d, 7=5.5 Hz, 2 H). MS calcd. for C25H16C12N4O3

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. 6271-78-9, 6-Chloropyridine-3-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BILOTTA, Joseph Anthony; CHEUNG, Adrian Wai-Hing; FIROOZNIA, Fariborz; GUERTIN, Kevin Richard; HAYDEN, Stuart; HAYNES, Nancy-Ellen; LUKACS-LESBURG, Christine M.; MARCOPULOS, Nicholas; MERTZ, Eric; QI, Lida; QIAN, Yimin; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2013/7676; (2013); 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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.Quality Control of 6-Bromopyridin-3-amine

Intermediate 51; 6-(2,6-Difluorophenyl)pyridin-3-amineIn a three neck round bottle flask, to a mixture of 1 ,3-difluorobenzene (23.24 mmol, 2.29 ml) in THF (30 ml) at -780C under argon atmosphere, a solution of n-BuLi (10.2 ml) in THF (2.5M) was added. The mixture was stirred at -78°C for 30 minutes and then it was heated to -5O0C. A solution of ZnCI2 (51 ml) in THF (0.5M) was added drop wise and the mixture was stirred at this temperature for 20 minutes. A solution of 6-bromopyridin-3-amine (11.56 mmol, 2.0 g) in THF (20 ml) and Pd(PPh3)4 (1.16 mmol, 1.3 g) were added respectively and the crude mixture was heated at 4O0C overnight. The solvent was evaporated and the crude mixture was purified by reverse phase chromatography eluting with a water-MeOH/AcN system affording 0.72 g (yield 30percent) of the expected product, delta 1H NMR (200 MHz, CDCI3): 3.83 (s, 2H), 6.95-7.00 (m, 2H), 7.06-7.09 (d, 1 H), 7.23- 7.32 (m, 2H)1 8.24 (s, 1 H). ESI/MS (m/e, percent): 207 [(M+1)\ 100].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6937-03-7, 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.6937-03-7, name is Methyl 2-aminoisonicotinate, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.

26 g of lithiumaluminum hydride was dissolved in 800 mL ofanhydrous THF. A solution of 103 g of methyl ether of2-aminoisonicotinate in 600 mL of anhydrous THFwas added at stirring and the formed slurry was boiledfor 3 h. After cooling water was carefully added, theprecipitate was filtered off and washed with 300 mL ofTHF. The combined filtrates were evaporated, theresidue was crystallized from benzene. Yield 61 g(73percent), mp 80?81.5°. 1H NMR spectrum (DMSO-d6),delta, ppm: 4.36 s (2), 5.19 s (1), 5.78 s (2), 6.40 d(1), 6.46 s (1), 7.81 d (1). 13 NMR spectrum(DMSO-d6), delta, ppm: 62.3, 105.2, 110.3, 147.7, 152.7,160.3. Found, percent: 57.63; 6.32; N 22.68. C6H8N2O.Calculated, percent: C 58.05; H 6.4; N 22.56.

Statistics shows that 6937-03-7 is playing an increasingly important role. we look forward to future research findings about Methyl 2-aminoisonicotinate.

Reference:
Short Survey; Lifshits; Ostapchuk; Brel; Russian Journal of Organic Chemistry; vol. 51; 5; (2015); p. 744 – 745; Zh. Org. Khim.; vol. 51; 5; (2015); p. 759 – 760,2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98400-69-2, 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. 98400-69-2, name is 4-(Boc-Amino)pyridine. A new synthetic method of this compound is introduced below.

8.1 1,1-Dimethylethyl (3,5-dibromopyrid-4-yl)carbamate A mixture of 1,1-dimethylethyl 4-pyridinecarbamate (11.0 g; 57.0 mmol) and N-bromosuccinimide (25.6 g; 142.0 mmol) in acetonitrile (50 ml) is heated for 12 hours at 55° C. The reaction mixture is concentrated under reduced pressure. The residue obtained is taken up in ether (400 ml), washed with saturated aqueous potassium bicarbonate solution (2*200 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue is chromatographed on a column of silica, eluding with an ethyl acetate/cylohexane gradient of from 0 to 10percent ethyl acetate. 8.2 g of 1,1-dimethylethyl (3,5-dibromopyrid-4-yl)carbamate are isolated in the form of a white solid. Yield (percent)=41

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98400-69-2, its application will become more common.

Reference:
Patent; Altenburger, Jean-Michel; Cremer, Gerard; Lassalle, Gilbert; Matrougui, Mostafa; US2003/207920; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19437-26-4, 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 19437-26-4 as follows.

General procedure: Two drops of glacial acetic acid as a catalyst were added to themixtures of thiosemicarbazides (0.5 mmol) and di(2-pyridyl) ketone,2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 8-hydroxy-2-quinolinecarboxaldehyde or 2-quinoxalinecarbaldehyde (0.5 mmol) in ethanol (5 ml). The glasstubes were sealed and placed into a microwave reactor at 83 C for20 min (the reactor power did not exceed 50W). The final productswere crystallized from dry methanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19437-26-4, its application will become more common.

Reference:
Article; Mrozek-Wilczkiewicz, Anna; Malarz, Katarzyna; Rejmund, Marta; Polanski, Jaroslaw; Musiol, Robert; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 180 – 194;,
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. 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, molecular formula is C12H10N2, 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. COA of Formula: C12H10N2

General procedure: Equimolar amounts of 1,10-diiodoperfluorodecane (1e) and dipyridyl 2a or its ethylene analogue 2b were dissolved in a vial containing chloroform at room temperature and in a vial. The open vial was closed in a cylindrical bottle containing paraffin oil. Chloroform was allowed to diffuse at room temperature and after two days 1e·2a,b were isolated as white crystals, washed with n-pentane, and characterized.

With the rapid development of chemical substances, we look forward to future research findings about 13362-78-2.

Reference:
Article; Catalano, Luca; Metrangolo, Pierangelo; Pilati, Tullio; Resnati, Giuseppe; Terraneo, Giancarlo; Ursini, Maurizio; Journal of Fluorine Chemistry; vol. 196; (2017); p. 32 – 36;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 941294-57-1, 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.941294-57-1, name is 5-Bromo-2-iodo-4-methylpyridine, molecular formula is C6H5BrIN, molecular weight is 297.92, as common compound, the synthetic route is as follows.

To a suspension of 5-bromo-2-iodo-4-methylpyridine(1g, 3.36 mmol) in NMP (6mL) with an inert atmosphere of argon, KF (0.585 g, 10.07 mmol), Cul (1.92 g, 10.08 mmol) and CF3SiMe3 (2.49 mL, 15.07 mmol) were added. The resulting solution was stirred overnight at 60C. After cooling, the mixture was poured into 12% aqueous ammonia, and then extracted with Et2O. The organic solutions were combined, dried over MgSO4, filtered and concentrated. Purification of the crude residue by normal phase chromatography (0% to 100%, hexane – diethyl ether) afforded the desired product (23% yield) as a yellow oil.

Statistics shows that 941294-57-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-iodo-4-methylpyridine.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Gonzalez Rodriguez, Jacob; Gual Roig, Silvia; Esteve Trias, Cristina; Vidal Gispert, Laura; EP2738172; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1003-68-5, 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 1003-68-5 as follows.

A mixture of Cul (0.19 g, 1 mmol), Cs2C03(6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100 C overnight, cooled to rt and filtered. The filtrate diluted with H20 (50 mL) was extracted with CH2C12(50 mL x 3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE / EtOAc (V / V) = 10 : 1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) m/z: 303.2 (M+l);-NMR (400 MHz, CDC13): delta 2.06 (s, 3 H), 3.16-3.32 (m, 4 H), 3.86-3.97 (m, 4 H), 4.44 (s, 2 H), 6.47 (d, 1 H, J = 9.6 Hz), 7.39-7.44 (m, 2 H), 7.48 (s, 1 H), 7.52-7.55 (m, 1 H), 7.99 (t, 1 H, J= 8.2 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem