Month: April 2022

Synthetic Route of 1221171-70-5, 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 1221171-70-5 as follows.

To a solution of 2-chloro-6-(trifluoromethoxy)pyridine (5.0 g, 25.3 mmol, 1 equiv) in MeOH (120 mL) was added triethylamine (7.7 g, 75.9 mmol, 10.5 mL, 3.00 eq) and Pd(dppf)Cl2 (930 mg, 1.27 mmol, 0.05 equiv). The suspension was degassed and purged with CO several times. The mixture was stirred at l00C under CO (50 Psi) for 48 hours. The reaction mixture was cooled to 20C and concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with PE/EtOAc = 10/1) to afford the title compound methyl 6-(trifluoromethoxy)picolinate as a yellow oil (3.85 g, 68% yield). LC-MS: m/z 222.0 (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,1221171-70-5, its application will become more common.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1221171-70-5, 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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below.

2-Bromo-6-trifluoromethoxypyridine (55); A solution of 2-chloro-6-trifluoromethoxypyridine (2, 7.0 g, 35.4 mmol) in hydrobromic acid (33% in acetic acid, 100 mL) was heated for 3 days at 100 0C. The reaction mixture was cooled down to 0 0C before being slowly neutralized by addition of saturated aqueous solution of sodium hydrogencarbonate (500 mL). After extraction with ethyl acetate (4 x 100 mL), the combined organic layers were dried over sodium sulfate before being evaporated. The crude oil was distilled under vacuum (67-69 0C / 15 mbar) to afford pure 2-bromo-6-trifluoromethoxypyridine (2, 4.2 g, 17.3 mmol, 48%) as a colorless oil.1H NMR (CDCl3, 300 MHz): delta = 7.58 (t, J = 7.9 Hz, 1 H), 7.37 (d, J = 7.7, 1 H), 6.92 (d, J = 8.0, 1 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.5 – 13C NMR (CDCl3, 75MHz): delta = 154.5, 141.0, 138.1, 125.1, 119.0 (q, J= 260 Hz), 110.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (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. 62150-47-4, name is Ethyl 4-bromopicolinate, molecular formula is C8H8BrNO2, 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. COA of Formula: C8H8BrNO2

At a temperature of less than 40 C,Dissolve 1300 g of Cpd 2 in 7 L of ethanol.Add 400g of sodium borohydride in batches,Stir at room temperature overnight;2N hydrochloric acid was added dropwise at a temperature of less than 20 C to adjust the pH to weakly alkaline,Rotate most of the ethanol,add water,Adjusted to strong alkaline with potassium carbonate,Extracted with ethyl acetate (EA),Wash the product to the aqueous phase with 1N hydrochloric acid.Extracted with EA,The aqueous phase is added with potassium carbonate to adjust to strong alkalinity,EA extraction, sodium chloride washing,Dry over anhydrous sodium sulfate and spin dry.Through the column, 4-bromopyridine-2-methanol (Cpd 3) 650 g was obtained. The yield was 62%.

With the rapid development of chemical substances, we look forward to future research findings about 62150-47-4.

Reference:
Patent; Tianjin Quan He Cheng Science And Technology Co., Ltd.; Song Yanmin; Wan Jiaqiang; Li Weide; (11 pag.)CN108516953; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 670253-37-9 ,Some common heterocyclic compound, 670253-37-9, molecular formula is C5H4ClIN2, 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.

In a one-neck round bottom flask, 90.7 g (357.1 mmol) of a 1F compound was added to 500 ml of NMP, and 21.4 g (182.1 mmol) of Zetan(CN)2 was added, followed by rapid addition of 41 g (35.7 mmol) of Pd(PPh3)4, 135 C reaction for 5h. The reaction was completed to give a brown oily liquid. The mixture was slowly poured into 3 L of ice water under stirring, and a large amount of a tan solid was precipitated, which was filtered, washed with water and dried to give Compound 1G

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,670253-37-9, its application will become more common.

Reference:
Patent; Chengdu Huajian Pending Technology Co., Ltd.; Zhang Lei; (14 pag.)CN109928968; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1440519-73-2, 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.1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, molecular formula is C15H13ClN2O2, molecular weight is 288.7289, as common compound, the synthetic route is as follows.

To a solution of 2-chloro-6-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo [3 ,4-b]pyridin-5-one (5.8 g, 20.0 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 1.7 g, 42.0 mmol) at room temperature. The resulting reaction mixture was stuffed for 30 mmbefore iodomethane (6.0 g, 42.0 mmol) was added. After stirring at room temperature overnight, the mixture was quenched with water and extracted with EtOAc. The organic layer was then washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the crude product which was then purified by flash column chromatography (silica gel 20 g, 5% to 20% ethyl acetate in DCM). The title compound was obtained (3.8 g, 57%) as a white solid. MS: 316.2 (M+Hj.

Statistics shows that 1440519-73-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LI, Dongbo; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; WU, Jun; ZHOU, Mingwei; WO2014/191336; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69422-72-6, 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.69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, molecular weight is 226.4446, as common compound, the synthetic route is as follows.

To 1.7 (1.0 g, 4.42 mmol, 1.0 eq) was added SOCl2(5.0 mL) followed by DMF (catalytic) and reflux ed for 16 h. Reaction mixture was concentrated under reduced pressure to obtain acyl chloride. Methyl hydrazine (0.20 g, 42.5 mmol, 1.0 eq) was dissolved in CH2C12(20.0 mL) followed by addition of solution of NaOH (0.72 g, 177 mmol, 4.0 eq) in water (5.0 mL). To the solution was added previously made acyl chloride solution in CH2C12(20.0 mL) dropwise. Reaction mixture was refluxed for 15 min. After completion of reaction, reaction mixture was transferred into water and extracted with CH2C12. Organic layers were combined, washed with brine, dried over Na2S04and concentrated under reduced pressure to pressure to obtain crude which was purified by column chromatography to provide 1.8. (1.1 g, 97.0 %). MS(ES): m/z 255.5 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 69422-72-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 188637-63-0, Adding some certain compound to certain chemical reactions, such as: 188637-63-0, name is (6-Bromopyridin-2-yl)methanamine,molecular formula is C6H7BrN2, 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 188637-63-0.

To an ice-cold solution of (R)-1-(tert-butoxycarbonyl)piperidine-3- carboxylic acid (1.09g, 4.75mmol) in 50 mL of CH2Cl2, 1-chloro-N,N,2-trimethyl-1- propenylamine (0.69mL, 5.3mmol) was added dropwise with stirring. The stirring was continued for 2 h at this temperature, then (6-bromopyridin-2-yl)methanamine (750 mg, 4.0mmol) was added, followed by 1.6 mL of iPr2NEt. The cooling bath was removed and the reaction mixture was stirred overnight at rt. After completion of the reaction monitored by HPLC, the reaction mixture was added to water (120 mL) and extracted with DCM (2 120 mL). The organic layer was washed successively with an aqueous solution of NaHCO3 (20 mL), water (20 mL), and brine (20 mL), then dried over Na2SO4 and concentrated under reduced pressure. The remaining residue was purified by flash column chromatography (ISCO eluted with Hexanes/EtOAC) to give 1.10g of desire title compound.

According to the analysis of related databases, 188637-63-0, the application of this compound in the production field has become more and more popular.

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; GREENLEE, William; (508 pag.)WO2017/35409; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: (R)-5-Amino-3-(5-bromo-2-fluoropyridin-3-yl)-3,6,6-trimethyl-3,6-dihydro-2H-1,4-thiazine 1,1-dioxide In an analogous sequence of reactions to those described for Example 7, steps 1-4, 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 50 5 mmol) was converted to the title compound in 20% yield. LC/MS (ESI+) m/z=364, 366 (M+H; 2 bromine isotopes).

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 1111637-74-1, 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 777931-67-6, 3-Bromo-2-chloro-6-methoxypyridine, 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, 777931-67-6, blongs to pyridine-derivatives compound. SDS of cas: 777931-67-6

D) 2-chloro-3-(2-fluoro-5-methoxyphenyl)-6-methoxypyridine Under an argon atmosphere, to a solution of 3-bromo-2-chloro-6-methoxypyridine (4.61 g) in toluene (60 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (3.52 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichlorome thane adduct (1.69 g) and 2.0 M aqueous sodium carbonate solution (31.1 mL), and the mixture was stirred at 80C for 1 hr. Water was added at room temperature, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.06 g) as a white amorphous solid. 1H NMR (300 MHz, DMSO-d6) delta 3.77 (3H, s), 3.91 (3H, s), 6.90-6.94 (1H, m), 6.96 (1H, d, J = 8.3 Hz), 6.98-7.06 (1H, m), 7.24 (1H, t, J = 9.1 Hz), 7.80 (1H, d, J = 8.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,777931-67-6, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; SHIBUYA, Akito; EP2816023; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 102645-33-0, 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.102645-33-0, name is 2,5-Dichloroisonicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.

To a solution of 2,5-dichloropyridine-4-carbaldehyde (2.75 g, 15.62 mmol) in DMSO (63 mL) was added /V-methyl-O-phenylenediamine (1.91 g, 15.62 mmol) and the mixture stirred at ambient temperature for 5 mins. Sulfur (500 mg, 15.62 mmol) was added and the mixture warmed to 60 C and allowed to stir for 2.5 hrs. The reaction was then cooled to R.T. and added to a bi-phasic stirred solution of DCM and water (200 mL ea). The resulting emulsion was extracted with DCM (3 x 100 mL) and the combined organics were washed with water (3 x 100 mL), dried over MgS04, filtered and stripped to a crude red gum which was purified by Biotage flash chromatography (45 M loaded with DCM, eluting with EtOAc / heptane 5-30 % over 10 CV, then holding for 5 CV) to afford the title compound (3.22 g, 74 %) as a pale orange solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.72 (s, 3 H) 7.26 – 7.35 (m, 1 H) 7.35 – 7.44 (m, 1 H) 7.69 (d, J=8.1 Hz, 1 H) 7.74 (d, J=8.1 Hz, 1 H) 7.95 (s, 1 H) 8.78 (s, 1 H). m/z (APCI+) for Ci3H9N3Cl2 278.05 / 280.00 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 102645-33-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; NAIR, Sajiv Krishnan; PLANKEN, Simon Paul; PLEWE, Michael Bruno; VERNIER, William Francois; YANG, Yi; ZHU, Huichun; WO2011/27249; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem