Tag: M.W:200-300

Application of 124236-37-9, 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. 124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate. A new synthetic method of this compound is introduced below.

[00173] Urea-H202 (161 mg, 1.72 mmol) was added into a solution of 56 (100 mg, 0.49 mmol) in DCE (4 mL). Trifluoroacetic anhydride (281 mg, 1.35 mmol) was added at -10 C for 2 h. The reaction mixture was stirred at 0 C for 2 h and then at rt overnight. The mixture was poured into ice-water (10 mL) and adjusted to pH 6-7 with 30% sodium hydroxide solution. The mixture was extracted with ethyl acetate (5 mL X 3). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated under reduced pressure to afford 57 (50 mg, 46%) as a yellow solid, which was used for the next step directly without further purification. LC-MS tR = 0.372 mm in 5-95AB_1.5 mm chromatography (Welch MK RP-18e 25-2mm), MS (ESI) m/z 221.8 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124236-37-9, Methyl 5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190319-62-0, 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 1190319-62-0 as follows.

Step 4: A solution of 6?-bromospiro[cyclopropane-l ,3?-pyrrolo[3,2-b]pyridin]-2?(1 H)-one (5.7 g, 24.6 mmol) in dry DMF (10 mL) was added dropwise to a stirred suspension NaH (60% dispersion in oil, 5.91 g, 148 mmol) in dry DMF (50 mL) under Ar at 0C. After complete addition, the mixture was stirred for 15 mm before dropwise addition of a solution of I ,2-dibromoethane (6.36 mL, 73.8 mmol) in dry DMF (10 mL).The brown reaction mixture was stirred at rt for 18 h. The mixture was reduced in volume and diluted with EtOAc (100 mL) and water (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2x 100 mL). The combined organic layer was washed with brine, dried over Na2SC4 and evaporated. Purification by column chromatography (silica, 33% EtCAc in heptane), followed by titruation from CH2CI2 afforded 6?-bromospiro[cyclopropane-l ,3?-pyrrolo[3,2-b]pyridin]-2?(1 ?H)-one (3.62 g,14.4 mmol, 58%) as a yellow solid. LCMS: calculated for [M+H]: 241, found: 241, isotope pattern present.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1190319-62-0, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2897-43-0, 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. 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine, molecular formula is C5H3Cl2N3O2, 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 2,6-dichloro-3-nitropyridin-4-amine in ethanol (150 mL) was added iron powder (14.3 g, 0.255 mol), water (46 mL), and then concentrated HCl (28 mL). The reaction mixture was then stirred at 95 C. for 16 hours, cooled to room temperature, and neutralized. The precipitates were collected by filtration and dried in vacuo. The crude product was then treated with water (200 mL) and extracted with EtOAc (3*200 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.85 g of the title compound (86.5% yield).

According to the analysis of related databases, 2897-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 182275-70-3, Adding some certain compound to certain chemical reactions, such as: 182275-70-3, name is 2-Iodo-6-methoxypyridine,molecular formula is C6H6INO, 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 182275-70-3.

(-)-P7C3-S243: (S)-N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline: (S)-9-(3- amino-2-fluoropropyl)-3,6-dibromo-9H-carbazole (72.2 mg, 0.18 mmol), 2-iodo-6-methoxypyridine 45.4 mg, 0.19 mmcl), copper iodide (2.9 mg, 0.015 mmcl) and cesium carbonate (119.4 mg, 0.36 mmcl) were added to an oven dried vial, which was nitrogen purged for 10 minutes. DMSO (0.36and 2,2,6,6-tetramethyl-3,5-heptanedione (4 il, 0.019 mmcl) were then added. The reaction was heated at 40 C for three hours. The cooled mixture was diluted with EtOAc and washed thrice witha solution of 9:1 saturated NH4CI: NH4OH and then thrice with water and then brine. The organic layer was dried over Na2SO4, filtered and concentrated. The well dried solid was dissolved in methylene chloride and passed through a short silica plug, which removed the small amount of unreacted amine. The filtrate was condensed to give white solid, which was purified by automated flash chromatography system in 50-80 % methylene chloride/hexanes. Isolated yield = 61%, ee =96%. Recrystallization to enhance ee was carried out by heating a solution of 15.8 mg of purified product in 1.0 ml of isopropanol. Overall Yield = 59 %, ee = 98.5 %1H NMR (CDCI3, 400 MHz) :5 8.16 (d, J = 1.9 Hz, 2H), 7.56 (d, J = 1.9 Hz, 2H), 7.35 – (t, J = 7.8 Hz, 1H),7.30 (d, J = 8.7 Hz, 1H), 6.04 (dd, J = 32.7, 8.0 Hz, 2H), 5.29 -5.02 (dm, 1H), 4.65 -4.46 (m, 3H), 3.87- 3.74 (m, 1H), 3.70 (s,3H), 3.66 – 3.49 (m, 1H). ESI m/z: 506.7 ([Mi-1], C22H19Br2FN2O requires504.98

According to the analysis of related databases, 182275-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF IOWA RESEARCH FOUNDATION; MCKNIGHT, Steven L.; READY, Joseph M.; PIEPER, Andrew A.; WO2015/70234; (2015); A3;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 914358-72-8, Adding some certain compound to certain chemical reactions, such as: 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine,molecular formula is C6H5BrClN, 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 914358-72-8.

A suspension of 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1,3,2-dioxaborolane) (0.836 g, 3.29 mmol), 5-bromo-3-chloro-2-methylpyridine (0.34 g, 1.65 mmol), potassium acetate (0.485 g, 4.94 mmol) in dioxane (5 mL) was degassed with a stream of argon for a couple of minutes. 1,1?-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.067 g, 0.08 mmol) was added and the mixture was heated at reflux under N2 for 1.5 h. The mixture was allowed to cool and filtered. The filter cake was washed with EtOAc. The filtrate was concentrated in vacuo and column chromatography using EtOAc 0% to 80% in heptane gave 442 mg (100%) of the title compound. 1H NMR (500 MHz, CDC13) delta ppm1.35 (s, 12 H), 2.65 (s, 3 H), 7.95 -8.03 (m, 1 H), 8.69 (d, 1 H); MS (ES+) mlz: 172 [M+C6H9]+

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. 914358-72-8, 5-Bromo-3-chloro-2-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; MINIDIS, Anna; RAHM, Fredrik; VIKLUND, Jenny; WO2013/54108; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 623585-74-0 ,Some common heterocyclic compound, 623585-74-0, molecular formula is C7H5Cl2NO2, 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 3N methylmagnesium bromide solution in ether (5.6 ml) was added dropwise to a mixture of methyl 2,5- dichloroisonicotinate (2.90 g) , iron (III) acetylacetonate (0.25 g) , THF (85 ml) and N-methylpyrrolidone (8.5 ml) under ice-cooling, and this was stirred at the same temperature for 1 hour. After an aqueous saturated sodium chloride solution (100 ml) was added to the reaction mixture, this was extracted with ethyl acetate, and the ethyl acetate layer was washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the desired product (1.82 g) as an oil.1H-NMR (CDCl3) delta 2.52 (3H, s) , 3.99 (3H, s), 7.74 (IH, s) ,8.34 (IH, s) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623585-74-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2006/64944; (2006); 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.83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.12, as common compound, the synthetic route is as follows.SDS of cas: 83664-33-9

6-Benzyloxy-pyridine-3-carbaldehyde To a solution of 2-benzyloxy-5-bromo-pyridine (1.64 g, 6.2 mmol) in tetrahydrofuran (25 mL, -78 C.) was added n-butyllithium (2.5 M in hexane, 2.61 mL, 1.05 equiv). After 1 h at -78 C., dimethylformamide (0.97 mL, 2 equiv) was added and the mixture stirred for 30 min. The reaction was quickly poured into a stirred solution of 5% aqueous sodium bicarbonate (50 mL) and extracted with diethyl ether (3*). The ethereal was washed with brine, dried over magnesium sulfate, and concentrated to give 1.16 g (quant.) which was used without purification. Mass spec.: 186.34 (MH)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83664-33-9, 2-(Benzyloxy)-5-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Chaturvedula, Prasad V.; Chen, Ling; Civiello, Rita; Conway, Charles Mark; Degnan, Andrew P.; Dubowchik, Gene M.; Han, Xiaojun; J. Jiang, Xiang Jun; Karageorge, George N.; Luo, Guanglin; Macor, John E.; Poindexter, Graham; Tora, George; Vig, Shikha; US2004/204397; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 777931-67-6, 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. 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, molecular formula is C6H5BrClNO, 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 round bottom flask was added 3-bromo-2-chloro-6-methoxypyridine (10.57 g), cyclopropyl boronic acid (4.28 g), palladium acetate (533 mg), (0887) tricyclohexylphosphine (1.33 g) and potassium phosphate (35.2 g). To this solid mixture was added toluene:H2O (158 mL; 9:1 ratio). The heterogeneous mixture was purged with a nitrogen stream for 1 min and then was heated at reflux overnight. The reaction mixture was diluted with EtOAc (100 mL) and water (100 mL). The phases were separated and the aqueous phase was backextracted twice with ethyl acetate (100 mL each). The combined organic phases were dried over magnesium sulfate and the crude residue was purified by flash chromatography (ethyl acetate / hexanes as the eluents) yielding 8.6 grams of 2-chloro-3-cyclopropyl-6-methoxypyridine as a colorless oil. LCMS method A: Rt = 0.61 min; (M+H)+ = 222.2, 224.2.1H NMR (CD3OD): delta 8.45 (s, 1H), 8.33 (s, 1H), 3.90-4.00 (m, 2H), 3.70-3.80 (m, 2H), 3.20-3.55 (m, 4H), 1.80-2.0 (m, 4H), 1.27 (s, 9H).

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 777931-67-6, 3-Bromo-2-chloro-6-methoxypyridine.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1039055-46-3, tert-Butyl (5-aminopyridin-2-yl)(methyl)carbamate, 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: C11H17N3O2, blongs to pyridine-derivatives compound. COA of Formula: C11H17N3O2

To 0.356 g (1.53 mmol) of the above amine in THF (3 mL) was added 0.70 mL of n-butyllithium (2.5 M solution in hexanes) and the mixture was stirred for 10 min. A solution of 0.21 g (0.52 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added, and the resulting mixture was stirred for 1 hr. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, and dried. The solvent was removed under vacuum, and the product mixture was purified by flash column chromatography, eluting with CH2Cl2/EtOAc (3:1), to give 0.075 g (13% yield) of tert-butyl 5-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]amino}-2-pyridinyl(methyl)carbamate, as a yellow powder: 1H NMR (DMSO-d6) delta 10.11 (s, 1H), 8.68-7.41 (m, 5H), 7.61 (d, J=9.0 Hz, 1H), 6.97 (d, J=8.1 Hz, 1H), 3.98 (s, 3H), 3.83 (s, 4H), 3.74-3.73 (m, 4H), 3.29 (s, 3H), 1.47 (s, 9H); LCMS (APCI+) m/z: 585 (MH+, 100%).

The synthetic route of 1039055-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pathway Therapeutics Limited; US2010/249099; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 64690-19-3, name is 4-(Octylamino)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 64690-19-3

6.18 g of 4-octylaminopyridine base and 3.15 g of 1,10-dichlorodecane were mixed, slowly heated to 120 C., exothermically reacted to 180 C., and thin layer chromatography (TLC) to confirm the reaction. 25 ml of dimethyformamide (DMF) was added and the mixture was warmed and completely dissolved again. The mixture was cooled to 0 C to precipitate crystals, which were filtered and dried under reduced pressure at 60 C. Through the above process, 7.3 g of 1,10-bisoctylaminopyridinium decane hydrochloride (Yield: 39.0%, mp 215 to 217 C) was obtained

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 64690-19-3, 4-(Octylamino)pyridine.

Reference:
Patent; Firson Co.,Ltd; Kim, Dong Jin; Koo, Chang Hwei; Park, Sung Yong; Cho, Ir Hwe; Lee, Sung Bae; Han, Dong Hoon; (12 pag.)KR2017/13425; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem