Day: March 24, 2022

Electric Literature of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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 solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn (CN) 2 (3.96 g, 33.7 mmol) and Pd (Ph3P) 4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30 ethyl acetate/hexanes to afford the product. 1H NMR (500 MHz, DMSO-d6) , delta 8.69 (s, 1H) , 7.50 (s, 1H) , 4.04 (s, 3H) LC/MS (M+1) + 169.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1235036-15-3 , The common heterocyclic compound, 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, 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 7A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate A solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate (1.00 g), EXAMPLE 1C (1.68 g) and cesium carbonate (2.56 g) was stirred together in N,N-dimethylacetamide (10 mL) at 110 C. overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (2*25 mL) and brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography using 1-30% ethyl acetate in hexanes provided the title compound.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Wang, Le; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96121; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-55-2, Adding some certain compound to certain chemical reactions, such as: 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine,molecular formula is C6H6FNO, 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 131747-55-2.

At 0C, 55% sodium hydride 0.70 g (16 mmol) was added in portions to a THF (20 mL) solution of (2-fluoropyridin-3-yl)methanol 1.3 g (10 mmol) synthesized in the same manner as in Reference Example 52 and iodomethane 6.6 mL (110 mmol), and the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (eluting solvent: hexane:ethyl acetate) to give the title compound 0.89 g (6.3 mmol, yield 63%) as a colorless oil. 1H-NMR spectrum (400MHz, DMSO-d6) delta:8.23 – 8.14 (m, 1H), 8.02 – 7.92 (m, 1H), 7.40 – 7.35 (m, 1H), 4.46 (s, 2H), 3.33 (s, 3H).

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. 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137778-20-2, 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 137778-20-2, name is 5-Bromo-6-methylpicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 10Methyl 5-bromo-6-methyl-2-pyridine carbonate synthesisInto a 500-l. glass-lined reactor was placed 5-bromo-6-methyl-2-pyridine carboxylic acid (30 kg, 138.9 moles) and methanol (133 kg, 4156 moles). The mixture was agitated and thionyl chloride (36.8 kg, 309.2 moles) was added while the temperature was maintained between 2030 C. After the addition, the mixture was heated to 5565 C. for 2 hrs. The reaction was stopped when the raw material was detected at less than 2%. Then solvent was removed by concentration at a temperature below 40 C. MTBE (280 kg) was added and the mixture was stirred for another 30 min. to dissolve the crude. Then the MTBE solution was transferred to one drum. To the above reactor was added water (300 kg). Then the solution containing the crude was pumped to the reactor while maintaining the reactor contents at 05 C. and stirred for 1 hr. After phase separation, the aqueous layer was extracted with MTBE (60 kg). The organic phases were combined, and concentrated at a temperature below 40 C. Hexane (60 kg) was added to the residue. The obtained solid was stirred, centrifuged and dried. White powder (22.36 kg, 97.2 moles) was obtained. The purity of the product was >98%, and the mole yield was 70%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 137778-20-2, 5-Bromo-6-methylpicolinic acid.

Reference:
Patent; Synergetica Changzhou Chemical Company; US2010/305330; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 92992-85-3, 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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To a mixture of (R)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (1 g),2-bromo-3,5-dimethylpyridine (975 mg),tris(dibenzylideneacetone)dipalladium(O)(92 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (125 mg) and tert-butoxy sodium (650 mg) was added toluene (17 mL) and the mixture was stirred under microwave irradiation at 130c for 2 hr. The reaction mixture was purified by column chromatography (hexane:ethyl acetate)to give the title compound (220 mg). MS (ESI)m/z: 306(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92992-85-3, 2-Bromo-3,5-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 823-61-0 ,Some common heterocyclic compound, 823-61-0, molecular formula is C7H10N2, 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.

To a solutionof 26-S3 (170 mg, 0.44 mmol) and 6-methylpyridin-2-amine (90 mg, 0.48 mmol) in DCE (5 mL) were added DIPEA (0.29 mL, 1.76 mmol) and EEDQ (217 mg, 0.88 mmol). The reaction mixture was stirred at 90 C overnight and concentrated under high vacuum. The remaining residue was purified by column chromatography on silica gel (eluted with PE/EtOAc = 4:1) to afford 26-S4(103 mg, 41% yield) as a yellow solid. LC/MS (ESI) m/z: 555/557 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-61-0, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 143803-93-4 ,Some common heterocyclic compound, 143803-93-4, molecular formula is C9H8N2O2, 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.

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

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. 143803-93-4, 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine, molecular formula is C7H8BrNO, 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.

Step AM2: 3-Bromo-5-bromomethyl-2-methoxy-pyridine To a solution of 3-bromo-2-methoxy-5-methyl-pyridine (Step AM3) (3.0 g, 14.7 mmol), was added NBS (3.1 g, 17.6 mmol) and AIBN (121 mg, 0.7 mmol) and the mixture was stirred at 80 C. for 1 h. H2O and CH2Cl2 were added and the phases were separated. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (heptane/EtOAc, 95:5?0:100). tR: 1.10 min (LC-MS 1).

According to the analysis of related databases, 717843-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Cotesta, Simona; Furet, Pascal; Guagnano, Vito; Holzer, Philipp; Kallen, Joerg; Mah, Robert; Masuya, Keiichi; Schlapbach, Achim; Stutz, Stefan; Vaupel, Andrea; US2013/317024; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-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, HPLC of Formula: C6H6INO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6INO

General procedure: A mixture of potassium fluoride (0.15g, 2.6mmol) and copper iodide (I) (0.50g, 2.6mmol) was heated under reduced pressure until a greenish color appeared, and after cooling to rt, an iodo compound (1.0mmol) in DMF/HMPA (2.5mL each) and trimethyl(trifluoromethyl)silane (0.38mL, 2.6mmol) were added to this flask successively. The mixture was stirred for the specified time and at the indicated temperature (see Table 2). After quenching with satd aqueous ammonium chloride, usual workup and purification by silica gel chromatography yielded the trifluoromethylated product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Article; Kawasaki-Takasuka, Tomoko; Yamazaki, Takashi; Tetrahedron; vol. 71; 38; (2015); p. 6824 – 6831;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

2-(2-CHLORO-4-NITRO-PHENOXYMETHYL)-PYRIDINE (2.4 g, 9.07 mmol) is suspended in MeOH (30 ML) and treated wet 5% Pt/C (Degussa type, ALDRICH, 0. 8 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is complete by TLC (ca 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MGS04) and concentrated to yield 1.7 g (7.23 mmol, 80%) of the desired product.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2004/46101; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem