Tag: M.W:200-300

Reference of 89466-18-2 ,Some common heterocyclic compound, 89466-18-2, 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.

Acetic anhydride (11.3 mL, 120 mmol) was added dropwise to formic acid (17.0 mL, 450 mmol) then stirred at room temperature for 24 minutes. The formic acid and acetic anhydride mixture was added to 6-bromo-2-methoxypyridin-3- amine (Y1) in 50 mL of THF via cannula. The reaction was stirred at room temperature for 30 minutes. An additional 10 mL of THF was used to aid the transfer. The reaction was stirred at room temperature for 2h. The reaction was quenched with 140 mL of ice cold water. This solution was then filtered leaving a white solid. The solid was rinsed with additional water, dried on the filter, then left under vacuum overnight to yield 5.04g (70%) of the formamide (Y2). 1H NMR (CDCI3 400 MHz) delta 8.45-8.43 (m, 2H), 7.61 (br s, 1 H), 7.08 (d, J = 8.0 Hz, 1 H), 4.03 (s, 3H). MS: M+1 = 231.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89466-18-2, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; ZHU, Zhaoning; GREENLEE, William, J.; LI, Hongmei; VICAREL, Monica, L.; QIN, Jun; DHONDI, Pawan, Kumar; HUANG, Xianhai; PALANI, Anandan; LIU, Xiaoxiang; SUN, Zhong-Yue; JOSIEN, Hubert B.; XU, Ruo; COLE, David, James; BURNETT, Duane, A.; BENNETT, Chad, E.; MCCRACKEN, Troy, M.; MACCOSS, Malcolm; WO2010/56722; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1604-14-4, 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. 1604-14-4, name is 2,6-Dichloro-isonicotinic acid ethyl ester, molecular formula is C8H7Cl2NO2, 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.

EXAMPLE 7E (2,6-dichloropyridin-4-yl)methanol To a solution of EXAMPLE 7D (3.1 g, 14.2 mmol) in ethanol (100 mL) at 0C was added sodium triacetoxyborohydride (2.7 g, 71.1 mmol) in portions and the mixture was heated at 80C for 3 hours. The mixture was concentrated and the residue was diluted with water (20 mL). I N Hydrochloric acid was added to quench excess sodiumtriacetoxyborohydride and then the mixture was neutralized with saturated aqueous sodium carbonate. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was recrystallized from methanol to give the title compound. MS: 178 (M + H+).

According to the analysis of related databases, 1604-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113682-56-7, Adding some certain compound to certain chemical reactions, such as: 113682-56-7, name is 1,4-Di(pyridin-4-yl)benzene,molecular formula is C16H12N2, 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 113682-56-7.

General procedure: Under an N2 atmosphere, a mixture of the imidazolium salt (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride, 2.2 mmol), the required N-heterocycle (1.0 mmol), PdCl2(2.2 mmol) and K2CO3(2.2 mmol) was stirred in anhydrous THF (10 mL) under reflux for 12 h. After cooling, filtration and evaporation, the residue was purified by preparative TLC on silica gel plates, eluting with CH2Cl2 to afford the corresponding dinuclear N-heterocyclic carbene-palladium(II) complexes 1-4.

According to the analysis of related databases, 113682-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Tao; Xu, Kai; Wang, Wanli; Zhang, Anan; Liu, Lantao; Transition Metal Chemistry; vol. 43; 4; (2018); p. 347 – 353;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1124382-72-4, 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. 1124382-72-4, name is 2-Amino-8-bromo[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C6H5BrN4, 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 the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 5C is added Et3N (11.6 mL, 83.3 mmol) followed by the appropriate acid chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and acid chloride (33 3 mmol) may be added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp, (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids may be collected by filtration, washed with H2O (2×50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the required intermediate (4). In some cases column chromatography (petrol/EtOAc) may be required to obtain pure compounds.

According to the analysis of related databases, 1124382-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 120034-05-1, 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.120034-05-1, name is Methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.

Example 30 – Preparation of Intermediate 7 [ 00261] The synthesis of Intermediate 7 followed General Procedure 8 following. General Procedure 8 Intermediate 5 Intermediate 7 [ 00262 ] To a round-bottomed flask charged with methyl 5-bromo-2-oxo- l,2-dihydropyridine-3-carboxylate (Intermediate 5, 50.0 g, 0.2154 mol, 1.0 eq) at 0 C under N2 atmosphere was added POCl3 (100 mL) dropwise. After 30 minutes the reaction mixture was warmed to 80 C and stirred for 12-15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured slowly into ice cold water. It was stirred for 30 min, at which point the product precipitated out as a white solid. The solid product was filtered and vacuum dried to give desired Intermediate 7 (40.0 g, yield-94.15%). m/z 252.12 [M+2]+ 1H NMR (DMSO-de, 400 MHz) delta 8.78 (d, J = 2.5 Hz, 1H), 8.50 (d, J = 2.5 Hz, 1H), 3.89 (s, 3H) ppm.

Statistics shows that 120034-05-1 is playing an increasingly important role. we look forward to future research findings about Methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, 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, 69045-84-7, blongs to pyridine-derivatives compound. Quality Control of 2,3-Dichloro-5-(trifluoromethyl)pyridine

EMBODIMENT 13: Preparation of ethyl 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-cyanoacetate To a 500 mL three-necked flask equipped with a thermometer was added 200 g DMSO, 25 g potassium hydroxide and 24 g ethyl 2-cyanoacetate. 44 g 2,3-dichloro-5-(trifluoromethyl)pyridine was added while the reaction temperature was controlled within 50 C. After addition, the reaction was continued for 1 hour. After the reaction was complete, the solvent was removed. Water was added. The mixture was acidified with hydrochloric acid, filtered, washed with water, dried to produce 85 g ethyl ethyl 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-cyanoacetate in 97% yield. 1H-NMR deltappm(CDCl3): 8.6(s, 1H), 6.27(s, 1H), 4.25(d, J=5.6 Hz, 2H), 3.40(br, 1H), 1.2 (t, J=5.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-84-7, its application will become more common.

Reference:
Patent; ZHEJIANG ZHUJI UNITED CHEMICALS CO., LTD; Su, Yehua; Shi, Jieping; Lu, Jianxin; Zhang, Tianhao; Yu, Xiaohua; Cai, Guoping; Chen, Bangchi; (7 pag.)US2017/369412; (2017); 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.1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.Safety of 5-Bromo-6-methoxypicolinic acid

A solution of 5-bromo-6-methoxypicolinic acid (3.24 g, 14.0 mmol, 1.1 equiv.) in DCM (63.5 mL) at ambient temperature was treated with a catalytic amount of DMF (7 drops) and oxalyl chloride (3.32 mL, 38.1 mmol, 3.0 equiv.). The resultant mixture was stirred at ambient temperature for 1 h at which point LCMS monitoring showed completion of the reaction. The mixture was concentrated, diluted with anhydrous THF (40.0 mL), concentrated again before being dried under high vacuum for 1 hour. The residue was diluted in anhydrous THF (40.0 ml), treated with triethylamine (6.18 mL, 44.4 mmol, 3.5 equiv.) and cooled toO C. A solution of(R)-2-(4-methoxybenzylamino)-2-(4- methylbenzofuran-2-yl)ethanol (3.95 g, 12.7 mmol, 1.0 equiv.) in THF (45.0 ml) was then quickly added and the resultant mixture was stirred at 0 C for 1 h. Volatiles were removed under vacuum and MeOH (80.0 mL) was added, followed by K2C03 (1.75 g, 12.7 mmol, 1.0 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours before water and EtOAc were successively added, layers were separated, and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography on silica (10- 50% EtOAc / hexanes) to afford the amide (4.58 g, 69%) as white foam. LCMS (ES+) [M+Hj+: 525.1/526.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 102368-13-8, 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 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one). This compound has unique chemical properties. The synthetic route is as follows.

b) (2,4-Dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester1 , 1 ‘-Thiocarbonyldi-2-pyridone (0.42 g, 1.8 mmol) was added to a mixture of (3-amino-2,4- dichloro-benzyl)-carbamic acid tert-butyl ester (0.50 g, 1.7 mmol) and dioxane (25 ml_) and stirred at rt for 2 h and at reflux for 2 d. The mixture was concentrated, diluted with DCM and filtered over silica gel. The filtrate was concentrated to give the sub-title compound.Yield: 0.49 g (86%). Rf = 0.83 (silica gel, DCM:EtOH 95:5).

According to the analysis of related databases, 102368-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; KUELZER, Raimund; MACK, Juergen; PFAU, Roland; STENKAMP, Dirk; PELCMAN, Benjamin; ROENN, Robert; LUBRIKS, Dimitrijs; SUNA, Edgars; WO2012/76672; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83004-10-8 ,Some common heterocyclic compound, 83004-10-8, molecular formula is C6H5Br2N, 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 mixture of isopropyl 3-oxopiperidine-l-carboxylate (4.50 g) and toluene (52 mL) was added pyrrolidine (2.59 g) at room temperature. The mixture was stirred at room temperature for 30 min, and concentrated. Toluene and CH3CN were added thereto, and the mixture was concentrated. The residue was mixed with CH3CN (52 mL) , and 2-bromo-6- (bromomethyl ) pyridine (7.32 g) was added thereto at room temperature. The mixture was heated under reflux for 15 hr, and the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.72 g) . MS: [M+H]+ 355.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83004-10-8, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52718-95-3, 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 52718-95-3, name is Methyl 2-bromonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Part D. Preparation of methyl 2-(3′-cyanophenyl)nicotinate. Methyl 2-bromonicotinate (2.0 g, 9.3 mmol) and 3-cyanophenylboronic acid (2.7 g, 18.4 mmol) were combined in 190 mL benzene. Sodium carbonate (19 mL of a 2 M aqueous solution), tetrabutylammonium bromide (152 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) chloride (325 mg, 0.5 mmol) were added. The entire mixture was evacuated to remove dissolved gasses, then placed under argon. The reaction was refluxed for 14 hours, diluted with water and EtOAc, separated, dried over Na2 SO4, filtered, and evaporated. The resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes) to yield a light yellow solid (1.70 g, 77%). 1 H NMR (CDCl3): delta 8.81 (dd, 1H, J=4.8, J’=1.8), 8.23 (dd, 1H, J=8.0, J’=1.9), 7.85 (s, 1H), 7.73 (m, 2H), 7.55 (t, 1H, J=7.7), 7.43 (m, 1H), 3.76 (s, 3H).

According to the analysis of related databases, 52718-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dupont Pharmaceuticals; US6060491; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem