Month: April 2022

Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

A sealed tube was charged with 16-1 (1.0 g, 2.70 mmol), Et3N (4.89 mL, 35.1 mmol) and Ethynyltrimethylsilane (4.85 mL, 35.1 mmol) and the resulting solution was degassed with Argon for about 10 minutes followed by the addition of CuI (514 mg, 2.70 mmol) and PdCl2(PPh3)2 (1.89 g, 2.70 mmol). The reaction tube was sealed and heated at 90oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was partitioned between heptane and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The crude mass was dissolved in MeOH (10 mL) and to it was added K2CO3 (713 mg, 5.16 mmol) and the solution was stirred at ambient temperature for 2 hours to produce 16-2. The reaction mass was filtered through a short bed of celite and the filtrate was concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-10% Ethyl acetate in Hexane) to afford 16-2 (462 mg, 1.46 mmol, 54%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.63 (d, J = 8.24 Hz, 1H), 7.43-7.28 (m, 10H), 7.34 (d, J = 8.16 Hz, 1H), 5.44 (s, 2H), 5.29 (s, 2H), 3.24 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33630-99-8, 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 33630-99-8 as follows.

To a mixture of 3-aminopyridin-2(1H)-one (3.25 g, 29.5 mmol) and sodium carbonate (6.26 g, 59.0 mmol) in tetrahydrofuran (100 mL) at rt was added benzylcarbonochloridate (5.27 mL, 36.9 mmol) over 5 mm. The mixture was stirred at rt for 24diluted with ethyl acetate (150 mL), and filtered through Celite. The filtrate was concentrated under vacuum to a volume of approximate 200 mL, washed with water (40 mL), and dried over anhydrous Mg504. The solution was concentrated under vacuum to a volume of approximate 50 mL. The precipitating material (the first crop of product) wascollected as a white solid by suction. The filtrate was concentrated under vacuum to almost dryness. The residue was stirred with diethyl ether (50 mL). The insoluble material (the second crop of product) was collected as a white solid by suction. The two crops of product was combined and dried at 50 C under vacuum to give the desired product, benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate (5.77 g, 23.62 mmol, 80 %yield), as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33630-99-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1026201-45-5, 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.1026201-45-5, name is 8-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.

SOCl2 (15 ml, 206 mmol) was added slowly to intermediate 39 (1.6 g, 6.6 mmol) while cooling on ice. The resulting solution was heated to reflux temperature for 4 h, and was then cooled to r.t. and concentrated in vacuo. The residue was triturated with DIPE and finally the product was dried. Yield: 1.7 g of intermediate 40 (99 %).

Statistics shows that 1026201-45-5 is playing an increasingly important role. we look forward to future research findings about 8-Bromoimidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); 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. 153374-33-5, name is 1-Methyl-1H-pyrrolo[3,2-b]pyridine, molecular formula is C8H8N2, 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. Recommanded Product: 153374-33-5

The reaction was conducted according to the General Procedure by heating KOt-Bu (4.5 mg, 0.04 mmol, 20 mol%), N-methyl- 4-azaindole 3a (26.4 mg, 0.2 mmol, 1 equiv), Et3SiH (98 muL, 0.6 mmol, 3 equiv) and 0.2 mL of THF at 45 C for 96 h. C2:C3 = 6:1. A mixture of C2- and C3-silylation products (16.2 mg, 33% yield) was obtained after purification by silica gel flash chromatography (50% EtOAc in hexanes). Analytically pure C2-silylation 4a was obtained as a colorless oil after subsequent purification by Preparative TLC (50% EtOAc in hexanes). Rf = 0.1 (33% EtOAc in hexanes); 1H NMR (500 MHz, CDCl3) delta 8.44 (dd, J = 4.6, 1.4 Hz, 1H), 7.60 (dt, J = 8.3, 1.2 Hz, 1H), 7.09 (dd, J = 8.3, 4.6 Hz, 1H), 6.90 (d, J = 0.9 Hz, 1H), 3.83 (s, 3H), 1.03- 0.97 (m, 9H), 0.96- 0.89 (m, 6H); 13C NMR (125 MHz, CDCl3) delta 147.0, 143.0, 142.7, 133.0, 116.4, 116.1, 113.8, 33.1, 7.6, 4.0. IR (Neat Film, NaCl) 2953, 2909, 2874, 1596, 1557, 1455, 1434, 1413, 1355, 1317, 1288, 1237, 1134, 1064, 1004, 800 cm-1; HRMS (ESI+) calc?d for C14H23N2Si [M+H]+: 247.1625, found 247.1621.

With the rapid development of chemical substances, we look forward to future research findings about 153374-33-5.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; GRUBBS, Robert, H.; FEDOROV, Alexey; TOUTOV, Anton; LIU, Wenbo; BETZ, Kerry; (129 pag.)WO2016/22624; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6515-09-9, 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To fuming HNO3 (136 rn) were added H2S04 (111 rn) and 23,6-trichoropyridine (24.2g, 133 mmo) at 0C. The reaction mixture was sHowed to warm to RT, then stirred at100C overnight. After cooing to 0C, the mixture was poured onto ice-water. Theunsoube materia was coHected by fitration to afford 2,3,6-trichoro-5-nitropyridine. Rt =1.07 mm (UPLC Method B2), 1H NMR (400 MHz, DMSO-d6) 6 ppm: 9.06 (s, IH).

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; PISSOT SOLDERMANN, Carole; QUANCARD, Jean; SCHLAPBACH, Achim; SIMIC, Oliver; TINTELNOT-BLOMLEY, Marina; ZOLLER, Thomas; (161 pag.)WO2015/181747; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-53-0, 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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

Methanesulfonyl chloride (0.15 mL, 1.96 mmol) was added to a 0 C cooled solution of [6-(trifluoromethyl)pyridin-2-yl]methanol (0.32, 1.78 mmol) and Et3N (0.30 mL, 2.13 mmol) in CH2Cl2 (15 mL). The reaction mixture was stirred at room temperature for 22 h and concentrated to dryness, rendering the title compound as a white sticky solid, which was used in the next step without further purification. HPLC-MS (Method H): Ret, 9.06 min; ESI+-MS m/z: 256 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-53-0, (6-(Trifluoromethyl)pyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; GOYA, Pilar; TORRENS-JOVER, Antoni; ALMANSA-ROSALES, Carmen; DIAZ-FERNANDEZ, Jose-Luis; CAAMANO MOURE, Ana; (347 pag.)WO2017/178510; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 175204-82-7, 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. 175204-82-7, name is Methyl 4-(trifluoromethyl)nicotinate. A new synthetic method of this compound is introduced below.

Step 2; In a 100 mL flask was placed 1.84 g (9.7 mmol, 1 eq) of methyl 4- trifluoromethylnicotinate in 25 mL of 1 M HCI in CHsCOOH. To this was then added 1.3 g of NCS (9.7 mmol, 1 eq) and the reaction allowed to. stir overnight. (18h). The mixture was then transferred to a 500 mL Erlenmeyer flask and to this was added 300 mL of 2 M HCI in Et20 with stirring. This resutted in a. white precipitate which was then filtered to provide 1.2 g (49%) of the desired 2-chloro-1-[4-(trifluoromethyl)-3- pyridinyl] ethanone hydrochloride as a white solid. 1H-NMR (DMSO-d6) No. 9. 21 (s, 1H), 9.02 (d, 1H), 7.94 (d, 1H), 5.19 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175204-82-7, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2003/72561; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116355-18-1, 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 116355-18-1 as follows.

The compound of example 146 (10 g, 47.4 mmol) was treated with pyridin-3-ylboronic acid (6.41 g, 52.1 mmol) in the presence of [1 ,1 ‘-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.77 g, 0.948 mmol) and sodium carbonate (7.53 g, 71 .1 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.2 g (83 %); 1H NMR (DMSO-de, 300 MHz): delta 2.2 (s, 3H, CH3), 7.49-7.57 (m, 3H, Ar), 7.70-7.84 (d, 1 H, J=8.1 Hz Ar), 7.90-7.92 (d, 1 H, J=7.5 Hz, Ar), 8.5 (s, 1 H, Ar), 8.6 (s, 1 H, Ar), 8.9 (s, 1 H, Ar); MS (ES+): m/e 210.1 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116355-18-1, its application will become more common.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); 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. 195044-14-5, name is 2-Bromo-6-tert-butylpyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C9H12BrN

Preparative Example P1Step 1 : Methyl 6-(tert-butvhpicolinate (P1a)To the solution of 2-bromo-6-(tert-butyl)pyridine (20.0 g, 93.9 mmol) in MeOH (100 mL) was added dppp (3.86 g, 9.39 mmol), Pd(OAc)2 (6.32 g, 9.39 mmol) and TauEpsilonXiAlpha (28.5 g, 281 mmol) and then the mixture was stirred under CO (4 MPa) at 70C for 12 h. The reaction mixture was filtered, concentrated and purified by CC (RhoEpsilonXi/EpsilonAlpha = 40/1) to give compound P1a (12.0 g, 66%) as a colorless oil.

The synthetic route of 195044-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-82-0, 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. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid, molecular formula is C7H6FNO3, 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.

In a round bottom flask, 5-fluoro-2-methoxy-nicotinic acid (150, 250 mg, 1.46 mmol) was combined with thionyl chloride (3.00 mL, 41.1 mmol) and the suspension was stirred at room temperature for 3 hours. The reaction was concentrated to dryness under vacuum to provide the desired compound, used in the next step without further purification.

According to the analysis of related databases, 884494-82-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon Inc.; Zhang, Jiazhong; Ibrahim, Prabha N.; Bremer, Ryan; Spevak, Wayne; Cho, Hanna; US9096593; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem