Tag: M.W:200-300

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. 95897-49-7, name is 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine. A new synthetic method of this compound is introduced below., name: 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of n-BuLi in hexane (2.5 M, 2 mL, 5.0 mmol, 0.54 equiv) and a solution of n-Bu2Mg in heptanes (1.0 M, 4.8 mL, 4.8 mmol, 0.53 equiv). The resulting solution was stirred for 10 min at RT (20 C). This was followed by the dropwise addition of a solution of 7-bromo-2H,3H-[1,4]dioxino[2,3-b]pyridine (2 g, 9.26 mmol, 1.00 equiv) in tetrahydrofuran (16 mL) with stirring at -10 C in 10 min. The resulting mixture was stirred for 1 h at -10 C. The reaction mixture was slowly added to a solution of thionyl chloride (16 mL) at -10 C. The resulting mixture was stirred for 0.5 h at -10 C. The reaction was then quenched by the careful addition of 30 mL of saturated ammonium chloride solution at 0 C. The resulting mixture was extracted with 3×50 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluting with ethyl acetate/petroleum ether (1:3). This provided 1.3 g (60%) of 2H,3H-[1,4]dioxino[2,3-b]pyridine-7-sulfonyl chloride as a white solid. LCMS m/z: calculated for C7H6ClNO4S: 235.64; found: 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, 95897-49-7, 7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ERICSSON, Anna; GREEN, Neal; GUSTAFSON, Gary; HAN, Bingsong; LANCIA, JR., David R.; MITCHELL, Lorna; RICHARD, David; SHELEKHIN, Tatiana; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; (140 pag.)WO2018/175474; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 118650-08-1, Adding some certain compound to certain chemical reactions, such as: 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate,molecular formula is C8H8BrNO2, 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 118650-08-1.

Step 3: To a round-bottom flask containing (5-bromo-pyridin-3-yl)-acetic acid methyl ester (40 mg, 0.17 mmol), 2-[4-(2′-fluoro-2-trifluoromethyl-biphenyl-4- yloxymethyl)-phenyl]-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane 13 (80 mg, 0.17 mmol), palladium acetate (6 mg, 0.026 mmol), 2-(dicyclohexylphosphino)biphenyl (18 mg, 0.051 mmol) and potassium fluoride (30 mg, 0.051 mmol) is added anhydrous 1,4-dioxane (2 ml). The flask is purged with argon and sealed. The mixture is stirred at 13O0C for 12 hours and then cooled to ambient temperature before water (5 ml) is added. The mixture is extracted with EtOAc (10 ml x 2), dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient) to give {5-[4-(2′-fluoro-2- trifluoromethyl-biphenyl-4-yloxymethyl)-phenyl]-pyridin-3-yl} -acetic acid methyl ester 14: LC-MS m/z: 496.0 (M+l).

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. 118650-08-1, Methyl 2-(5-bromopyridin-3-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2007/24922; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-86-7, 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 153034-86-7, name is 2-Chloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-chloro-4-iodopyridine (4.943 g, 20.6 mmol) and formic acid(88%, 10 mL) was stirred at 105 C. for 21 h. The excess of formic acid was removed in vacuo, and the mixture was quenched with 2 M aq Na2CO3, extracted with 0H2Cl2, dried over Na2SO4. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel eluted with CH2Cl2/MeOH to afford 1.716 g (38%) of 4-iodopyridin-2(1H)-one as a solid. LC-MS Method 1 tR=0.82 min, m/z=222 (MH+); 1H NMR (400 MHz, (0D3)2SO) delta 7.14 (d, J=6.5 Hz, 1H), 6.87 (s, 1H), 6.49 (d, J=7.0 Hz, 1H).

According to the analysis of related databases, 153034-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, 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 5-bromo-6-methoxypyridine-2-carboxylic acid (500 mg, 2.15 mmol, 1 eq) in sulfuric acid (10 mL) in ice bath was added HNO3 (5 mL) dropwise. The solution was stirred at 60 C for 16 h. After cooling to rt, the solution was poured into ice/water (20 mL). The solids were collected by filtration to provide 3-amino-5-bromo-6-methoxypyridine-2-carboxylic acid as a light yellow solid (260 mg, 44%). LCMS (ES) [M-l]” m/z 275.0.

According to the analysis of related databases, 1214334-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; YU, Ming; XU, Qing; ZANCANELLA, Manuel; (246 pag.)WO2019/36377; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-81-9 ,Some common heterocyclic compound, 884494-81-9, molecular formula is C6H5BrFNO, 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.

3,5-Dimethyl-isoxazole-4-sulfonic acid 4-(5-fluoro-2-methoxy-pyridin-3-yl) benzylamide Di-tert-butyl dicarbonate (3.5 g, 16 mmol) and triethylamine (13 ml, 9.4 mmol) were added to a stirred solution of 4-aminomethylphenylboronic acid (3 g, 16 mmol) in tetrahydrofuran (100 ml). The reaction was stirred under reflux for 1 hour, then the solvent evaporated and the residue partitioned between water and ethyl acetate. The organic phase was concentrated under reduced pressure to give tert-butoxycarbonylaminomethyl-4-phenyl-boronic acid (2.67 g, 10.6 mmol) as a white solid. Toluene (16 ml), ethanol (4 ml), 2M sodium carbonate solution and tetrakis(triphenylphosphine) palladium (0) were added to tert-butoxycarbonylaminomethyl-4-phenyl-boronic acid (1.349 g, 5.4 mmol) and 3-bromo-5-fluoro-2-methoxy-pyridine (0.505 g, 2.45 mmol) and the mixture stirred under reflux for 24 h. Water was added and the mixture extracted with ethyl acetate. The organic phase was separated and the solvent evaporated. The residue was purified on silica gel eluting with 3:1 heptane/ethyl acetate to give [4-(5-fluoro-2-methoxy-pyridin-3-yl-benzyl]-carbamic acid-tert-butyl ester as a yellow oil. Trifluoroacetic acid (2 ml, 0.026 mmol) was added to a solution of [4-(5-fluoro-2-methoxy-pyridin-3-yl-benzyl]-carbamic acid-tert-butyl ester (0.8 g, 2.41 mmol) in dichloromethane (4 ml) and the reaction mixture stirred for 2 h. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic phase was separated and the solvent evaporated to give 4-(5-fluoro-2-methoxy-pyridin-3-yl)-benzylamine. The title compound was prepared in a similar manner to N-[1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-3,4-difluoro-benzenesulfonamide (Example 34) using 4-(5-fluoro-2-methoxy-pyridin-3-yl)-benzylamine and 3,5-dimethyl-isoxazole-4-sulfonyl chloride. MS (ESI) m/z: 392 [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. 884494-81-9, 3-Bromo-5-fluoro-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); 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. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, 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. Recommanded Product: 2-Bromo-6-methoxypyridin-4-amine

In a 50 mL single collar flask 500 mg (2.4 mmol, 1 eq) of 2 bromo-6-methoxy-pyridin-4- ylamine were introduced, to which was added 20 mL of toluene and 586 mg (4.92 mmol, 2 eq) of thionyl chloride, and the mixture heated at reflux for 3 hours. The reaction medium was dry concentrated under vacuum, and the residue was returned to solution in 20 mL of acetonitrile. 325 mg (2.46 mmol, 1 eq) of 2-hydroxy-2-methyl-pentanoic acid was then added at ambient temperature. After 16 hours at ambient temperature, the reaction mixture was heated to 80C for 4 hours, then to 60C for 3 days, and the reaction mixture was then dry concentrated. The residue was dissolved in 50 mL ethyl acetate. The solution was washed twice with 50 mL of an aqueous solution saturated with ammonium chloride, and then twice with 50 mL of water. The organic phase was then dried over magnesium sulphate and then dry concentrated under vacuum. A brown oil was obtained which was purified by chromatography on silica with a 1/1 (v/v)heptane/ethyl acetate mixture as the eluent. A brown solid was then obtained and purified by chromatography on grafted C18 silica with a water / acetonitrile mixture as the eluent (gradient 5 at 100% acetonitrile). 2-Hydroxy-2-methyl-pentanoic acid (2-bromo-6- methoxy-pyridin-4-yl)-amide was obtained in the form of a white solid. Melting point = 122C. NMR (1H, DMSO): 0.9 (t; 3H; J=4 Hz); 1.1 -1.3 (m; 1 H); 1.4 (s; 3H); 1.4-1 .5 (m; 1 H); 1.6 (m; 1 H); 1 .7 (m; 1 H); 3.9 (s; 3H); 5.8 (s; 1 H); 7.4 (d; 1 H; J=1 .4 Hz); 7.8 (d; 1 H; J=1 .4 Hz); 10.2 (s; 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 1196152-34-7.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; POINSARD, Cedric; WO2013/64681; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1152617-24-7, 3-Chloro-4-iodopyridin-2-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, Product Details of 1152617-24-7, blongs to pyridine-derivatives compound. Product Details of 1152617-24-7

Step b: To a solution of 3-amino-5-chloropyrazine-2-thiol (100 mg, 0.619 mmol), 3-chloro-4-iodopyridin-2- amine (315 mg, 1.238 mmol), XantPhos (35.8 mg, 0.062 mmol), and Pd2(dba)3 (28.3 mg, 0.03 mmol) in dioxane (3 mE) was added (at RT and under N2) DIPEA (324 IL, 1.856 mmol). The resulting solution was stirred in a microwave reactor for 2.5 h at 100 C. After cooling to RT, the reaction was diluted with EtOAc and it was filtered through a pad of Celite with EtOAc (10 mE). The combined filtrates were concentrated and the resulting residue was purified by silica chromatography (0 to 5% gradient of MeOH/DCM) to give 3-((2-amino-3-chloropyridin-4-yl)thio)-6-chloropyrazin-2-amine (180 mg, 0.627 mmol). ?H NMR (400 MHz, METHANOE-d4) oe ppm 7.88 (s, 1H), 7.68 (d, J=5.56 Hz, 1H), 6.06 (d, J=5.56 Hz, 1H), 1.35-1.43 (m, 2H). MS mlz288.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1152617-24-7, 3-Chloro-4-iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131803-48-0 ,Some common heterocyclic compound, 131803-48-0, molecular formula is C8H8BrNO2, 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 tert-butyl 4-(N-phenylsulfamoyl)piperazine-1-carboxylate (0.600 g, 1.757 mmol) in N,N-dimethylformide (10 mL) was slowly added sodium hydride (60.00 %, 0.091 g, 2.285 mmol) at the room temperature, and the mixture was stirred for 5 min at the same temperature. The reaction mixture was treated with methyl 6-(bromomethyl)nicotinate (0.485 g, 2.109 mmol), and stirred at the same temperature for additional 16 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (SiO2, 40 g cartridge; ethyl acetate / hexane = 10 % to 50 %) to give the crude product, which was dissolved in hexane (100 mL), and stirred. The resulting precipitates were collected by filtration, washed by hexane, and dried to give tert-butyl 4-(N-((5-(methoxycarbonyl)pyridin-2-yl)methyl)-N-phenylsulfamoyl)piperazine-1-carboxylate as white solid (0.585 g, 67.9 %).

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. 131803-48-0, Methyl 6-(bromomethyl)nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; MIN, Jaeki; BAE, Miseon; KIM, Dohoon; JIN, Seokmin; KYUNG, Jangbeen; (191 pag.)WO2017/18805; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-40-5, 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. 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide, molecular formula is C9H12BrNO2, 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.

27G. Methyl (4-(6-(l-((tert-butoxycarbonyl)amino)but-3-en-l-yl)-2-oxo-l,2- dihydropyridin-4-yl)-3-nitrophenyl)carbamate: To a solution of 27F (3.0 g, 7.15 mmol) and l-(2-ethoxy-2-oxoethyl)pyridinium bromide (1.189 g, 7.15 mmol) in EtOH (130 mL), was added ammonium acetate (11.03 g, 143 mmol) portion wise. After 15 min, the mixture was stirred at 75 C. The reaction mixture was then concentrated and dissolved in EtOAc. The organic layer was then washed with 1.0 N HC1, H20, saturated sodium bicarbonate solution and finally by brine. The organic phase was dried over sodium sulfate, filtered and concentrated to yield a residue which was purified by normal phase chromatography to isolate the desired product (2.2 g, 67%) as a brown solid. MS (ESI) m/z: 459.3 (M+H)+.

According to the analysis of related databases, 17282-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAM, Patrick Y.S.; CLARK, Charles G.; CORTE, James R.; EWING, William R.; GILLIGAN, Paul J.; JEON, Yoon; YANG, Wu; SMITH, Leon, M., II.; WANG, Yufeng; WO2013/22814; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1033201-61-4, name is 6-Amino-3-bromopicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-3-bromopicolinic acid

A slurry of 6-amino-3-bromopicolinic acid (25 g) in 400 mL 1:1dichloromethane/chloroform was added to nitrosonium tetrafluoroborate (18.2 g) in dichloromethane(100 mL) at 5 oc over 1 hour. The resulting mixture was stirred for another 30 minutes, then warmed30 to 35 oc and stirred overnight. The reaction was cooled to room temperature, and then adjusted to pH4 with aqueous NaH2P04 solution. The resulting solution was extracted three times withdichloromethane, and the combined extracts were washed with brine, dried over sodium sulfate,filtered and concentrated to provide the title compound

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, 1033201-61-4, 6-Amino-3-bromopicolinic acid.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; SOUERS, Andrew, J.; PHILLIPS, Andrew, C.; JUDD, Andrew, S.; BRUNCKO, Milan; (717 pag.)WO2017/214282; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem