Day: June 16, 2021

Electric Literature of 58481-11-1, 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. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, 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.

In a dried flask was zinc powder (3.05 g, 46.69 mmol) suspended in anhydrous tetrahydrofuran (25 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.168 mL, 1.95 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.2 mL, 1.58 mmol) was added and stirred at room temperature for 1 h 15 min. Then, 4-(bromomethyl)-2-fluoro-1-(trifluoromethyl)benzene (10 g, 38.91 mmol) in tetrahydrofuran (5 mL) was added in 6 equal portions every 10 minutes under ice-cooling. After complete addition the ice-bath was removed and the reaction mixture stirred at room temperature for 18 h. Then was stirring switched off to let the solids settle. The supernatant was used in next transformation. To a solution of methyl 2-chloroisonicotinate (5.15 g, 30 mmol) and Pd(PPh3)4 (0.693 g, 0.60 mmol) in tetrahydrofuran (40 mL) under nitrogen in a dried flask was added freshly prepared (3-fluoro-4-(trifluoromethyl)benzyl)zinc(II) bromide (12.55 g, 38.91 mmol) in tetrahydrofuran (50 mL). The resulting bright yellow mixture was heated to 60° C. for 2 h 20 min, then cooled to room temperature. The reaction was quenched by the addition of 10percent NH4Cl. It was diluted with ethyl acetate. After phase separation, the organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was suspended in 150 mL MTBE and sonicated, then the yellow insolubles were filtered off and washed with MTBE. The volume of the filtrate was increased to ca. 200 mL, then hydrogen chloride (7.50 mL, 30.00 mmol) (4M in dioxane) was added dropwise. A colorless precipitate formed. The resulting suspension was stirred for ca. 1 h, then sonicated for 2 min. The formed solid was collected and washed with MTBE and dried. The solid was dissolved in DCM and washed with 10percent K2CO3. After phase separation, the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate (8.26 g, 88percent) was isolated as a pale orange oil. 1H NMR (400 MHz, cdcl3) delta 3.94 (s, 3H), 4.24 (s, 2H), 7.06-7.18 (m, 2H), 7.52 (t, 1H), 7.69-7.75 (m, 2H), 8.68-8.75 (m, 1H). MS m/z 314 (M+H)+

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Intermediate 153-Bromo-4-chloro-1H-pyrazolo[4,3-c]pyridineN-bromosuccinimide (1.87 g, 10.5 mmol) was added to a solution of Intermediate 11 (1.61 g, 10.5 mmol) in acetonitrile (50 ml), and the mixture was heated to reflux for 3 h. The solvents were evaporated and DCM (60 ml) was added to the crude solid and the mixture stirred at r.t. for 30 min. The beige solid was filtered off, washed with DCM, then dried under vacuum (1.98 g, 81percent). 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.69 (d, J=6.0 Hz, 1 H), 8.22 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 232 / 234 / 236 [M + H]+.

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, 871836-51-0, 4-Chloro-1H-pyrazolo[4,3-c]pyridine.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; MCIVER, Edward, Giles; SMILJANIC, Ela; HARDING, Denise, Jamilla; HOUGH, Joanne; WO2010/106333; (2010); 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 875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4BrN3

Step 1 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (Compound 4-2) Sodium hydride (720 mg, 30 mmol) was added into a 100 ml reaction flask, and anhydrous THF (40 mL) was added to the reaction flask. After stirring at 0 C. for 5 min, the reaction substrate 5-bromo-1H-pyrazolo[3,4-b]pyridine (4.0 g, 20 mmol, commercially available) was dissolved in THF (20 ml), and the resulting solution was slowly added dropwise to the reaction flask through the constant pressure funnel, and stirred for 30 min. Afterwards, iodomethane (1.6 ml, 26 mmol) was added dropwise to the reaction system. After completion of the addition, the reaction solution was slowly warmed to room temperature and stirred overnight. The reaction progress was monitored by TLC. After completion of the reaction, 10 ml of ice water was added to the reaction system to quench the reaction, THF was removed by concentration under reduced pressure, and the residue was extracted with dichloromethane (60 ml) and water (20 ml*3). The organic layer was dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 4.1 g brown solid, which was separated and purified by Combi-flash chromatography [PE:EA=10:90-40:60] to give the title compound 4-2 (3.1 g, 73%). MS m/z (ESI): 211.9 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 875781-17-2.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

2,4,6-Trichloropyridine (5 g, 27.4 mmol) in anhydrous THF (100 ml) was cooled to -78 C. A solution of n-butyllithium (22.27 ml, 28.8 mmol) (1.6M in hexane) was added slowly at -78 C. The solution was stirred at -78 C. for 30 mins, then treated with a solution of ethyl formate (10.15 g, 137 mmol) maintaining an internal temperature below -74 C. The resulting solution was stirred at -78 C. until all starting material was consumed (monitored by TLC, 9:1 heptane/EtOAC), then it was quenched at -78 C. with a solution of saturated ammonium chloride and 50 ml 0.5N aq. HCl under vigorous stirring. It was then allowed to warm to r.t. The quenched mixture was extracted with EtOAc, the organic phase was washed with brine, dried over MgSO4, and concentrated. The crude residue (light yellow solid) was purified by flash chromatography on silica gel with 0-20% EtOAc/heptane to provide 5.1 g (88% yield) of the desired 2,4,6-trichloronicotinaldehyde as a white solid. 1H NMR (400 MHz, chloroform-d3) delta ppm=10.42 (s, 1H), 7.45 (s, 1H).

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BARBE, Guillaume; BEBERNITZ, Gregory Raymond; GENG, Sicong; GULGEZE EFTHYMIOU, Hatice Belgin; LIAO, Lv; MA, Fupeng; MO, Ruowei; PARKER, David Thomas; PENG, Yunshan; PEUKERT, Stefan; YAMADA, Ken; YASOSHIMA, Kayo; (78 pag.)US2018/111932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 142266-62-4, 2,5,6-Trichloronicotinamide, 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, SDS of cas: 142266-62-4, blongs to pyridine-derivatives compound. SDS of cas: 142266-62-4

Oxalyl chloride (2 M in DCM. 1.73 mL, 3.46 mmol) was added to a mixture of 2,5,6-trichloronicotinamide (0.710 g, 3.15 mmol, Intermediate P) in tetrahydrofuran (16 mL); the mixture was stirred at 65 C. for 30 min. The reaction mixture was poured into a flask containing 6-isopropyl-N4,N4-bis(4-methoxybenzyl)pyrimidine-4,5-diamine (1.236 g, 3.15 mmol), and the reaction mixture was stirred at RT for 15 min. The reaction mixture was diluted with EtOAc (150 mL), added to a separatory funnel, and washed with saturated, aqueous sodium bicarbonate (2*100 mL); the organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo to give N-((4-(bis(4-methoxybenzyl)amino)-6-isopropylpyrimidin-5-yl)carbamoyl)-2,5,6-trichloronicotinamide (2.30 g, 3.57 mmol, >99% yield) as an amber foam. MS (ESI, +ve) m/z: 642.7/644.8 (M+1)+.

The synthetic route of 142266-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

An aqueous sodium hypochlorite solution (5% chlorine, 43 mL) was added to a solution of 5-bromopyridin-3-ol (5.0 g) and sodium hydroxide (1.3 g) in water (50 mL) at room temperature, and the mixture was stirred overnight. After addition of an additional aqueous sodium hypochlorite solution (5% chlorine, 10 mL), the mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with acetic acid, and the resulting precipitate was collected by filteration to give the title compound (4.54 g) as a light brown solid, which included 5-bromo-2,4-dichloropyridin-3-ol as a byproduct. The solid was subjected to the next reaction without further purification. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.49 (1H, s), 8.06 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 74115-13-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; KINA, Asato; EP2848622; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929617-35-6, 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. 929617-35-6, name is 5-Bromo-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4BrN3, 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.

General procedure: To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in DMF (5 mL), K2C03(875 mg, 6.345 mmol) was added. After 10min, ferf-butyl 3-bromopropylcarbamate (724 mg, 3.045 mmol) was added and the reaction mixture was heated at 60C for 26h. The reaction mixture was cooled to RT, poured into ice water and extracted with EtOAc (2 x100 mL). The organic layer was washed with brine solution (2 x 20 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated to dryness. The crude compound was triturated with n-pentane to afford the title compound (200 mg, 27%) as a yellow solid. LC-MS (method 1): Rt = 2.15 min; m/z = 354.18 (M+H+).

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 929617-35-6, 5-Bromo-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13535-01-8 ,Some common heterocyclic compound, 13535-01-8, molecular formula is C5H5BrN2, 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 solution of 3-amino-5-bromo pyridine (XX) (1.0 g, 5.78 mmol) in dry pyridine (10 mL) was added pivaloyl chloride (XXI) (769 mg, 6.38 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction was poured into an ice water/saturated aqueous NaHCO3 mixture and stirred for 30 min. The precipitate was filtered, washed with cold water and dried at room temperature to yield N-(5-bromopyridin-3-yl)pivalamide (XXII) as an off- white solid (1.082 g, 4.22 mmol, 73.1% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.23 (s, 9H), 8.37 (d, J=2Hz, 1H), 8.39 (t, J=2Hz, 1H), 8.80 (d, J=2Hz, 1H), 9.58 (brs, 1H); ESIMS found C10H13BrN2O m/z 258.9 (Br81M+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. 13535-01-8, 5-Bromopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100366-75-4 ,Some common heterocyclic compound, 100366-75-4, molecular formula is C6H3F3IN, 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.

Intermediate 36: 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride Step (i): [5-(Trifluoromethyl)pyridin-2-yl]methanol To the solution of 2-iodo-5-(trifluoromethyl)pyridine (CAS number 100366-75-4; 10 g, 69.4 mmol) in toluene (250 ml) at -78 C. was added n-BuLi in hexane (2.5 M, 15.0 mL, 37.5 mmol). The reaction was stirred at -78 C. for 15 minutes. To this was then added drop wise DMF (3.5 ml) and then stirred at -78 C. for 1 hour. Sodium borohydride (2.74 g, 72.0 mmol) and methanol (50 ml) were added and the resulting reaction mixture was stirred for 30 minutes and then allowed to warm to room temperature. The reaction was cooled to -10 C. and to this was then added a saturated solution of ammonium chloride. The organics were extracted with ethyl acetate (2×200 ml) and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound which was used without further purification. 1H NMR (400 MHz, DMSO) delta ppm 4.66-4.65 (m, 2H), 5.69-5.66 (m, 1H), 7.71-7.69 (m, 1H), 8.23-8.21 (m, 1H), 8.87 (s, 1H) MS ES+: 178

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. 100366-75-4, 2-Iodo-5-trifluoromethylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 910543-72-5 , The common heterocyclic compound, 910543-72-5, name is 3-Amino-5-bromo-1-methylpyridin-2(1H)-one, molecular formula is C6H7BrN2O, 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.

vii. The compound 9 (1.0 eq) was dissolved in DCM, then methanol(0.01eq) and glacial acetic acid(0.01eq) were added to facilitate dissolution. After stirring a little while, the HCHO or CH3CHO liquid was added slowly. The reaction mixture was stirred at room temperature for 0.5 hour. After the reaction was completed by TLC detection, Na(CN)BH3 (3.0 eq) was added into the reaction mixture, the reaction lasted for 1 hour. Then the mixture were evaporated under reduced pressure to remove the solvent and the residual methanol, and the obtained crude product was extracted with EA/H2O/brine, dried. Intermediate 10 was gained. The yield was 60%.

The synthetic route of 910543-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rong, Juan; Feng, Zhan-Zhan; Shi, Yao-Jie; Ren, Jing; Xu, Ying; Wang, Ning-Yu; Xue, Qiang; Liu, Kun-Lin; Zhou, Shu-Yan; Wei, Wei; Yu, Luo-Ting; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem