Month: April 2022

Application of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below.

25 mL of anhydrous THF was placed under nitrogen and cooled to -78 C. 2.2 ml (5.5 mmol) of a 2.5 M solution of n-butyl lithium in hexanes were added. To the resulting solution was slowly added 0.7 mL (1.4 g, 5.8 mmol) of 1,3-dibromobenzene. Upon complete addition the resulting solution was stirred at -78 C. for 90 min. 1.00 g (5.71 mmol) of 3-trifluoromethyl-pyridine-2-carbaldehyde was added rapidly. The dark solution was warmed to -20 C. and stirred for 20 min at that temperature. The resulting mixture was distributed between 10% aqueous citric acid and dichloromethane. The phases were separated and the aqueous layer extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and the solvent completely evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 1.053 g (3.171 mmol, 58%) of (3-bromo-phenyl)-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta 8.84 (m, 1H), 8.18 (dd, 1H), 7.63 (m, 1H), 7.53 (dd, 1H), 7.42 (m, 1H), 7.26-7.24 (m, 2H), 6.31 (d, 1H), 6.02 (d, 1H),; MS: m/z 332.0+334.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-62-1, its application will become more common.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256805-54-5, 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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

Trimethylaluminum (7.6 mL, 2.0 M in toluene, 15 mmol) was added slowly to a 0 C. mixture of 6-chloro-4-methoxypyridin-3-amine (2.4 g, 15 mmol) and propionitrile (1.16 mL, 16.1 mmol). The flask was removed from the ice bath, allowed to warm to rt over 5 min, then was stirred at 105 C. for 17 hours. The mixture was cooled to 0 C. and THF (15 mL) was added very slowly followed by water (1 mL), 15 wt % aqueous NaOH (1 mL) and water (3 mL), stirring for 10 min after each addition. The resulting mixture was allowed to warm to rt over 30 min with stirring, then Celite was added, and the mixture stirred an additional 30 min. The mixture was then filtered through Celite with THF and concentrated. The residue was diluted with water and the pH adjusted to pH 1-2 by the addition of 1 N aqueous HCl. The solution was then washed twice with EtOAc and the aqueous layer pH adjusted to pH 10-11 by the addition of 1 N aqueous NaOH. The aqueous solution was then extracted four times with DCM, the organic layers combined, dried with anhydrous Na2SO4, filtered and concentrated to provide the title compound, which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Tanis, Virginia M.; Woods, Craig R.; Fourie, Anne M.; Xue, Xiaohua; (120 pag.)US2019/382354; (2019); 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. 34206-49-0, name is 5-Bromopyridine-2,3-diol, the common compound, a new synthetic route is introduced below. COA of Formula: C5H4BrNO2

To a solution of 5-bromopyridine-2,3-diol (10 g, 53.19 mmol, 1 eq.) in DMF (250 mL) atroom temperature was added K2C03 (21 g, 159.57 mmol, 3 eq.) followed by 1,2-dibromoethane(5.5 mL, 63.82 mmol, 1.2 eq.) dropwise. The resulting mixture was stirred at 100C overnight.Progress of reaction was monitored by TLC. After the completion, reaction mixture was cooledto room temperature, diluted with ice cold water (300 mL) and extracted with DCM (3 x300 mL).Combined organic layer was washed with brine and dried over anhydrous sodium sulphate.Removal of solvent under reduced pressure afforded crude was purified by Combi-Flash on silica gel using methanol-dichloromethane (0-50 %) as eluents to afford 7-bromo-2,3-dihydro- [1,4]dioxino[2,3-b]pyridine (2.9 g, 25.26%).LCMS: 215 [M+1]

The synthetic route of 34206-49-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1452-94-4, 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 1452-94-4, name is Ethyl 2-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To ethyl 2-chloronicotinate (15.0 g, 81 mmol) in anhydrous N, N-dimethylacetamide (75 ml) was added zinc cyanide (5.71 g, 48.6 mmol), Pd2 (dba) 3 (742 mg, 0.81 mmol), zinc (636 mg, 9.72 mmol), and 1, 1’BIS (diphenylphosphino) ferrocene (898 mg, 1.62 mmol), and the resulting mixture heated at 120 C for 1 hour. The mixture was cooled to room temperature and partitioned between water (300 ml) and diethyl ether (150 ml), the mixture was filtered through Celiez and the phases separated. The aqueous phase was further extracted with diethyl ether (2 x 100 ml), the combined diethyl ether layers washed with saturated NACI, dried over NA2SO4, FILTERED and evaporated to give the title compound (14.26 g, 100%).

According to the analysis of related databases, 1452-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13958-85-5, 3-Fluoro-5-methylpyridin-4-amine, 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: C6H7FN2, blongs to pyridine-derivatives compound. COA of Formula: C6H7FN2

General procedure: Pd2dba3 (8.25 mg, 9.01 pmol), XantPhos (13.0 mg, 22.5 pmol) and Cs2C03 (110 mg, 0.34 mmol) were dissolved in DMF (2.25 mL) in a sealed tube while N2 was bubbling. 1-49 (42.0 mg, 0.25 mmol) and 1-1 (53.5 mg. 0.23 mmol) were added and the reaction mixture was stirred at room temperature for 10 min. Then, the reaction mixture was heated at 110 C for 20 h. The reaction mixture was cooled to room temperature, filtered through Celite and washed with EtOAc. The solvent was removed under reduced pressure and the crude mixture was purified by reverse phase column chromatography (mobile phase: HCOOH (0.l%)/(MeCN:MeOH, 1 :1), gradient from 95:5 to 63:37) to afford compound 91 (42 mg, 50%) as a white solid.

The synthetic route of 13958-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; LEENAERTS, Joseph, Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; MARTINEZ LAMENCA, Carolina; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (110 pag.)WO2019/243533; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8, 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

B) Synthesis of 2- (pyridin-2-yl)-2-bromomethyl-4-hydrox methyl-1, 3-dioxolane cisltrans 316 ml of glycerol were dissolved in 2 1 of toluene and 13.6 g of p- toluenesulfonic acid and 195 g of 2-bromoacetyl-pyridine hydrobromide were added to this solution. The reaction mixture was refluxed for 24 hours, with removal of the water present in the azeotrope. Once the mixture had cooled to ambient temperature, 2 1 of 5% NaHCO3 were added, the two-phase mixture was stirred for 5 minutes and the phases were then separated. The aqueous phase was extracted six times with 600 ml of toluene, the organic phases were combined, dehydrated with Na2S04, and evaporated to dryness under reduced pressure, giving rise to 80 g of (cis/trans)-2-(pyridin-2-yl)-2-bromomethyl-4- hydroxymethyl-1,3-dioxolane (yield 42%).

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 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; ITALFARMACO S.P.A.; WO2005/40156; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51173-05-8, 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. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine, molecular formula is C5H4FNO, 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.

Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM showed 4-80 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEt A different product was obtained. No desired product in these extracts.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique; US2005/209246; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211532-15-8, 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. 1211532-15-8, name is 6-Methoxy-5-(trifluoromethyl)nicotinic acid, molecular formula is C8H6F3NO3, 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.

N,O-dimethylhydroxylamine hydrochloride (4.3 g), N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride(9.5 g), and N,N-diisopropylethylamine (30 mL) were added to a mixture of 6-methoxy-5-(trifluoromethyl)nicotinicacid (7.8 g) and methylene chloride (80 mL) under ice-cooling, and then the reaction mixture was stirred at room temperaturefor 17 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were addedethyl acetate and water, followed by stirring for 30 minutes. The mixture was extracted with ethyl acetate, the organiclayer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residuewas purified by silica gel column chromatography (hexane-ethyl acetate) to N,6-dimethoxy-N-methyl-5-(trifluoromethyl)nicotinamide (5.0 g) as an oil.

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 1211532-15-8, 6-Methoxy-5-(trifluoromethyl)nicotinic acid.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; TANAKA, Hiroaki; AKAIWA, Michinori; NEGORO, Kenji; MIHARA, Hisashi; FUJI, Hideyoshi; TAKAMATSU, Hajime; (133 pag.)EP3196200; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-46-4, 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.

Crude tert-butyl ((4aRS,11bRS)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (70 mg, 0.165 mmol) was suspended in DMF (2 ml) and sonicated for 1 min. 5-Chloro-3-methylpyridine-2-carboxylic acid (34.0 mg, 0.198 mmol), pyridine (0.04 ml, 0.496 mmol) and HATU (94 mg, 0.248 mmol) were added and resulting suspension was stirred for 45 min at RT. The mixture was diluted with EtOAc (8 ml) and saturated NaHCO3 solution (3 ml). Water was added to dissolve precipitated solids. The organic layer was separated, washed with water and concentrated, and the resulting concentrate/residue was purified by FC on 12 g RediSep Gold column using 10-80% EtOAc in heptane to afford tert-butyl ((4aRS,11bRS)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (76 mg, 0.132 mmol, 80% yield) as white solid.

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 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

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

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. HPLC of Formula: C5H2Cl3N

A mixture of 2,3,6-trichloropyridine (18.2 g, 0.1 mol)Pd / C (10%) (2.73 g),1-isopropyl-4-methylcyclohexene (69 g, 0.5 mol) was added to methanol (182 g)Slowly heated to 60 C for 4 hours;After the reaction,The methanol was distilled off by distillation and vacuum distillation,Add water (100 g),The mixture of 2,3-dichloropyridine and water was distilled off by steam distillation at atmospheric pressure,Cooled by filtration to obtain 2,3-dichloropyridine 14g,Purity (HPLC) ?98%Yield 95%.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Patent; Jiangsu Zhongbang Pharmaceutical Co., Ltd.; Qian, Yong; Xu, Qiang; Gao, Qian; Zhao, Huayang; Zhang, Xiaoqing; (5 pag.)CN106518754; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem