Day: March 23, 2022

Reference of 90993-26-3, 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.90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.

Step 2: 7-bromo-lH-imidazo[4,5-c]pyridine 5-oxide To a stirred solution of 7-bromo-lH-imidazo[4,5-c]pyridine (1.0 g, 5.05 mol) and chloroform (20 mL) was added m-chloroperoxybenzoic acid (2.83 g, 12.6 mmol) and the reaction mixture stirred for 30 min at RT. The reaction mixture was filtered, washed with chloroform (10 mL), and the white solid was dried under high vacuum. The solid resulting solid was dissolved in a dichloromethane and methanol mixture, absorbed onto celite and purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% methanol in dichloromethane with 3% triethylamine) affording 7-bromo-lH- imidazo[4,5-c]pyridine 5-oxide as a white solid (580 mg, 54%) used as is in the next step.

Statistics shows that 90993-26-3 is playing an increasingly important role. we look forward to future research findings about 7-Bromo-1H-imidazo[4,5-c]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135124-71-9, 5-(Hydroxymethyl)nicotinonitrile, 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, Safety of 5-(Hydroxymethyl)nicotinonitrile, blongs to pyridine-derivatives compound. Safety of 5-(Hydroxymethyl)nicotinonitrile

Compound I-2-3 (2.0 g, 14.91 mmol) was added to a 50 mL single-mouth bottle.Add thionyl chloride (6.5mL),After dichloromethane (20 mL) was reacted at room temperature for 3 h,The reaction was completed by TLC, the reaction system was spun dry, and the oil pump was dried to obtain compound I-2-4.The yield was 1.8 g, and the yield was 79.4%.

The synthetic route of 135124-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Dankang Pharmaceutical Biological Co., Ltd.; Xu Yong; Lin Dang; Huang Lu; Hu Hai; (36 pag.)CN110092779; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89364-04-5, 3-Bromo-4-nitropyridine, 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, Recommanded Product: 3-Bromo-4-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 3-Bromo-4-nitropyridine

To a solution of 1,4-dioxane (60mL) and water (10mL) was added 3-bromo-4-nitropyridine (1.02g, 5.0mmol), (4-bromophenyl)boronic acid (1.10g, 5.5mmol), Pd(PPh3)4 (0.23g, 0.2mmol), and Na2CO3 (1.33g, 12.5mmol). Then the reaction was allowed to stir at reflux temperature (110C) for 18h. The reaction was cooled down, poured into water (40mL) and extracted with EtOAc (80mL×3). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in reduced pressure. The residue was purified by silica gel column chromatography using an eluent (10:90 EtOAc/hexanes) to afford a yellow solid product 1 (1.0g, 72%). Rf=0.50 (1:2 EtOAc/hexanes), mp 135-137C. 1H NMR (CDCl3): delta 7.21 (d, J=8.0Hz, 2H, Ph-H), 7.61 (d, J=8.0Hz, 2H, Ph-H), 7.68 (d, J=5.2Hz, 1H, Py-H), 8.78 (s, 1H, Py-H), 8.84 (d, J=5.2Hz, 1H, Py-H). 1H NMR (DMSO-d6): delta 7.41 (dt, J=2.2, 9.0Hz, 2H, Ph-H), 7.71 (dt, J=2.2, 9.0Hz, 2H, Ph-H), 8.03 (d, J=5.5Hz, 1H, Py-H), 8.87 (s, 1H, Py-H), 8.93 (d, J=5.5Hz, 1H, Py-H). MS (ESI): 279 ([M+H]+, 100%).

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 25; 15; (2015); p. 2953 – 2957;,
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. 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Recommanded Product: 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone

A mixture of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 51 mmol), (R)-2-methylpropane-2-sulfinamide (12.2 g, 101 mmol) and titanium (IV) ethoxide (26.1 mL, 126 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, brine was added and the mixture was stirred for 10 min. The suspension was filtered through silica gel. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0-20% EtOAc/hexanes) gave (R,Z)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (16 g, 50 mmol, 99% yield) as a bright yellow oil. LC/MS (ESI) m/z=321 (M+H).

The synthetic route of 1111637-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Step 1: Synthesis of methyl 3-(6-bromo-4-methylpyridin-2-yl)-3-hydroxycyclobutanecarboxylate A solution of 2,6-dibromo-4-methylpyridine (1.50 g, 5.97 mmol) in DCM (30 mL) was cooled to -78 C., and n-BuLi (2.5 M, 2.60 mL, 6.56 mmol) was added dropwise to the above solution at -78 C. The solution was stirred at -78 C. for another 15 min. Methyl 3-oxocyclobutanecarboxylate (917 mg, 7.16 mmol) was added to the solution, and the resultant mixture was stirred at -78 C. for 30 min. The mixture was then quenched by addition of saturated aqueous NH4Cl solution and extracted with DCM. Organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column (PE:EA=2:1) to give methyl 3-(6-bromo-4-methylpyridin-2-yl)-3-hydroxycyclobutanecarboxylate (1.0 g, 56%) as a white solid, MS (ES+) C12H14BrNO3 requires: 299, found: 300 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73112-16-0, 2,6-Dibromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Kim, Joseph L.; Kevin, Douglas J.; Brubaker, Jason D.; (57 pag.)US2017/267661; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206981-49-8, 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. 1206981-49-8, name is 3-(Trifluoromethoxy)pyridin-2-amine, molecular formula is C6H5F3N2O, 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 3-(trifluoromethoxy)pyridin-2-amine (300 mg, 1.68 mmol) in dichloromethane (8 mL) was added N-bromosuccinimide (450 mg, 2.53 mmol) at 20 C. The reaction mixture was stirred at the same temperature for another 5 mm and subsequentlyconcentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether) affording product (220 mg, 5 1%): 1H NMR (400 MHz, DMSO-d6) oe: 8.03 (d, I = 2.0 Hz, 1H), 7.75 – 7.74 (m, 1H), 6.68 (brs, 2H).

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 1206981-49-8, 3-(Trifluoromethoxy)pyridin-2-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4 ,Some common heterocyclic compound, 29241-65-4, molecular formula is C6H3BrClNO2, 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.

Sulfuric acid (2 mL, 52.1 mmol) was added to the suspension of 5-bromo-2-chloronicotinic acid (1) (12.3 g, 52 mmol) was in methanol (100 mL). The mixture was stirred and refluxed for 15 hours. The solvent was evaporated and the residue was neutralized with saturated aqueous NaHC03(aq.). The result suspension was filtered and the solid was washed by water and dried by pump. Methyl 5-bromo-2-chloronicotinate (2) (11.6 g, 89 % yield) was afforded. NMR (400 MHz, CDCL) delta 8.53 (d, J = 2.4 Hz, 1H), 8.25 (d, J = 2.4 Hz, 1H), 3.93 (s, 3H). 13C NMR (101 MHz, CDCL) delta 163.58, 152.75, 148.61, 142.49, 127.64, 118.57, 53.10. ESI-MS m/z: 251.9 (M+H+).

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. 29241-65-4, 5-Bromo-2-chloronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; ZHAO, Xue, Zhi; SMITH, Steven; METIFIOT, Mathieu, A.; JOHNSON, Barry; MARCHAND, Christophe; HUGHES, Stephen; POMMIER, Yves; BURKE, Terrence, R.; WO2014/186398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-41-6, 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. 131747-41-6, name is 2-(Trifluoromethyl)isonicotinic acid. A new synthetic method of this compound is introduced below.

A solution of 616 2-(trifluoromethyl)isonicotinic acid (10.0 g, 52.4 mmol) in 20 tetrahydrofuran (150mL) was cooled to 0 C., 1 mol/L 617 borane-tetrahydrofuran solution (105 mL, 105 mmol) was addedunder a nitrogen atmosphere and the mixture was stirred at 75 C. for 2 hr. The reaction mixture was pouredinto ice water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and driedover sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressureand the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the618 title compound ( 5.60 g , 31.6 mmol, 60%). MS (ESI) m/z 178 (M+H)+ 1H NMR (300 MHz, CDCl3): delta 8.68 (d, J=4.8 Hz, 1H), 7.79 (s, 1H), 7.64 (d, J=4.8 Hz, 1H) . 5.62 (br-s,1H), 4.66 (s, 2H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-41-6, 2-(Trifluoromethyl)isonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; EA PHARMA CO., LTD.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; KAWAHIRA, Mizuki; FUJII, Tomohiro; SUGIKI, Masayuki; OHSUMI, Koji; OKUZUMI, Tatsuya; (285 pag.)US2016/332999; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 886365-46-4

To a solution of Intermediate 12 (100 mg, 0.195 mmol) in N,N-dimethylformamide (1.0 mL) was added 5-chloro-3-methylpicolinic acid (43.6 mg, 0.254 mmol), (O-(7-azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate) (111 mg, 0.293 mmol), and pyridine (0.047 mL, 0.586 mmol). The reaction was stirred at ambient temperature for 2 hours, and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was redissolved in DCM (0.5 mL) and TFA (0.301 mL, 3.91 mmol) was added. The reaction was stirred at RT for an hour. The reaction was quenched with saturated aqueous sodium carbonate, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica-gel column chromatography, eluting with 0-50% (3:1 ethyl acetate:ethanol, 2% ammonium hydroxide) in heptanes, to provide the title compound (62 mg, 68.2% yield). 1H NMR (400 MHz, DMSO-d6) ppm 1.28-1.34 (m, 1H) 1.46 (s, 3H) 1.68-1.72 (m, 1H) 1.74 (s, 3H) 1.87-2.09 (m, 2H) 2.57 (s, 3H) 3.68 (d, J=5.77 Hz, 1H) 6.03 (br. s., 2H) 7.17 (dd, J=11.74, 8.90 Hz, 1H) 7.72-7.81 (m, 1H) 7.81-7.89 (m, 1H) 8.03 (dd, J=2.25, 0.68 Hz, 1H) 8.52-8.61 (m, 1H) 10.54 (s, 1H). LC/MS (ESI+) m/z=465.1 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 886365-46-4.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58236-70-7, 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. 58236-70-7, name is 5-Bromo-3-chloropyridin-2(1H)-one, molecular formula is C5H3BrClNO, 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.

36.0 g (172.7 mmol) of 5-bromo-3-chloro-2-hydroxypyridine are stirred at 160° C. for 6 hours in 320 ml of phosphorus tribromide. The reaction mixture is cooled to room temperature and poured carefully into ice water. After 2 hours, the mixture is extracted three times with 500 ml of dichloromethane in each case. The combined organic phases are washed with sodium bicarbonate solution until neutral, dried over Na2 SO4 and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/dichloromethane) gives 20.53 g of 3-chloro-2,5-dibromopyridine. STR14 m.p.: 40°-41° C.

According to the analysis of related databases, 58236-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem