Month: April 2022

Application of 867279-13-8, 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 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4,4,5,5-Tetramethyl- [1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H pyrrole-2- carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv. ) and 4-bromo-2- chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv. ) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2C03, Pd (PPh3)4 (108 mg, 0.094 mol, 0.2 equiv. ) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2S04, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/ water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+ 433.0, ES- 431.0).

According to the analysis of related databases, 867279-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/100342; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1190862-70-4, Adding some certain compound to certain chemical reactions, such as: 1190862-70-4, name is Ethyl 5-bromo-6-methylnicotinate,molecular formula is C9H10BrNO2, 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 1190862-70-4.

16A: Ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate : A degassed solution of ethyl 5-bromo-6-methylnicotinate (600 nig, 2.458 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (874 mg, 3.44 mmol), potassium acetate (374 mg, 3.81 mmol) and PdCl2(dppf)-CH2Cl2 adduct (161 mg, 0.197 mmol) in dioxane (10 mL) was heated to 60 C with vigorous mixing ON. The reaction mixture was concentrated onto Celite, then purified by flash chomatography utilizing a 40g ISCO column and eluting with 0-90% EtOAc in hexanes. The pure fractions were concentrated to afford ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (490 mg, 1.599 mmol, 65.0 % yield) as a waxy white solid. MSESI m/z 291.8 (M+H)

According to the analysis of related databases, 1190862-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MERTZMAN, Michael E.; DZIERBA, Carolyn Diane; GUERNON, Jason M.; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; SPERGEL, Steven H.; (245 pag.)WO2019/89442; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885168-20-7, 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 885168-20-7, name is 2-Bromo-5-fluoro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. Preparation of 2-(benzylthio)-5-fluoro-4-methylpyridine To a mixture of 2-bromo-5-fluoro-4-methylpyridine (25.0 g, 131.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.0 g, 3.3 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.8 g, 6.6 mmol) in anhydrous 1,4-dioxane (260 mL) was added N,N-diisopropylethylamine (34.4 mL, 197 mmol) and benzyl mercaptan (14.6 mL, 125 mmol). The reaction mixture was carefully degassed with nitrogen and then heated at 100 C. for 16 hours. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. After addition of water (50 mL) to the residue, the mixture was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate under reduced pressure and purification of the residue by column chromatography, eluting with a gradient of 0 to 30% of ethyl acetate in heptane, afforded the title compound as colorless oil (28.0 g, 91% yield): 1H NMR (300 MHz, DMSO-d6) delta 8.38 (d, J=1.5 Hz, 1H), 7.38 (dd, J=8.1, 1.5 Hz, 2H), 7.27-7.22 (m, 4H), 4.38 (s, 2H), 2.22 (d, J=0.9 Hz, 3H); MS (ES+) m/z 234.2 (M+1).

According to the analysis of related databases, 885168-20-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xenon Pharmaceuticals Inc.; Andrez, Jean-Christophe; Burford, Kristen Nicole; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Jia, Qi; Lofstrand, Verner Alexander; Wesolowski, Steven Sigmund; Wilson, Michael Scott; US2020/71313; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53636-70-7, 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.53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid, molecular formula is C8H7NO4, molecular weight is 181.1455, as common compound, the synthetic route is as follows.

EXAMPLE 14 A mixture of 6-methylpyridine-2,3-dicarboxylic acid (19.75 g) and acetic anhydride (51 ml) was stirred and heated in an oil bath (bath temperature 110 C.) for 5 hours. The solvent was removed in vacuo and a 2:1 mixture of dichloromethane and ether was added, giving a dark brown solid. A solution of this solid in dichloromethane was passed through a pad of silica gel, eluding with dichloromethane, and the solvent was then evaporated to give partially purified 6-methylpyridine-2,3-dicarboxylic acid anhydride (12.1 g).

Statistics shows that 53636-70-7 is playing an increasingly important role. we look forward to future research findings about 6-Methyl-2,3-pyridinedicarboxylic acid.

Reference:
Patent; Knoll Aktiengesellschaft; US5935973; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 699-98-9, 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 699-98-9, name is 2,3-Pyridinedicarboxylicanhydride. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of phthalic anhydride in THF (1.0 mm), TMSA (4.0 equiv.) was added and the mixture was refluxed with stirring for 30 h. The resulting solution was concentrated in vacuo until a solid formed. The solid was washed with diethyl ether (5×4 ml) to obtain high purity imidazolin-2-ones 3.

According to the analysis of related databases, 699-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lopez, Hector S.; Enciso, Jose E.; Ochoa-Teran, Adrian; Velazquez, Juan I.; Sarmiento, Juan I.; Mendeleev Communications; vol. 26; 1; (2016); p. 69 – 71;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15103-48-7, Adding some certain compound to certain chemical reactions, such as: 15103-48-7, name is Pyridine-2-sulfonic acid,molecular formula is C5H5NO3S, 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 15103-48-7.

Preparation 99 To a solution of 4-hydroxy-1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1-one (0.78 g) and triethylamine (2 ml) in DMSO (10 ml) was added a solution of pyridinesulfonic acid (1.16 g) in DMSO (4 ml) at room temperature. After being stirred for 20 minutes at the same temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1M-HCl, water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.22 g). MS (m/z): 334 (M+ +1) IR (Nujol): 1735, 1690 cm-1 NMR (CDCl3, delta): 2.38 (3H, s), 2.40 (3H, s), 2.97 (2H, t, J=6.4 Hz), 3.47 (2H, t, J=6.4 Hz), 7.17-7.26 (4H, m), 7.53-7.59 (4H, m), 9.88 (1H, s)

According to the analysis of related databases, 15103-48-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5972965; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-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, Quality Control of 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-3-(difluoromethoxy)pyridin-2-amine

To a mixture of 5-bromo-3-(difluoromethoxy)pyridin-2-amine (1.00 g, 4.18 mmol) in EtOH (10.0 mL) was added 2-bromo-l, l-di ethoxy ethane (1.07 g, 5.44 mmol, 818 uL) and HBr (7.45 g, 30.4 mmol, 5.00 mL, 33% in HOAc), and the mixture was stirred at 90 C for 16 h. The mixture was concentrated under reduced pressure to remove EtOH, and the residue was dissolved into ethyl acetate (50.0 mL) and washed with NaHC03 (50 mL) and brine (50.0 mL). The organic layer was dried with Na2S04, then concentrated under reduced pressure to give 6-bromo-8-(difluorom ethoxy )imidazo[l,2-a]pyri dine (900 mg, 3.42 mmol, 82% yield) as a brown solid. LC-MS (ESI+) m/z 265.1 (M+H)+; 1HNMR (400 MHz, MeOD): d 8.67 (s, 1 H), 7.98 (d, 1 H), 7.67 (s, 1 H), 7.29 (s, 1 H), 7.46 – 7.10 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); 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. 1256811-02-5, name is 1-(5-Bromo-2-methoxypyridin-3-yl)ethanone, 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. Recommanded Product: 1256811-02-5

To a solution of l-(5-bromo-2-methoxypyridin-3-yl)ethanone (2.0 g, 8.69 mmol) in HBr (20 mL, HO Ac solution), Br2 (1.4 g, 8.76 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. Then the reaction mixture was filtered to collect the HBr salt. The solid was suspended with Na2C03 solution, extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to provide 2-bromo-l-(5-bromo-2- hydroxypyridin-3-yl)ethanone (2.0 g, yield: 74%). 1H- MR (DMSO, 400 MHz) delta 12.83 (br s, 1H), 8.11-8.13 (m, 2H), 4.85 (s, 2H). MS (M+H)+: 295.

With the rapid development of chemical substances, we look forward to future research findings about 1256811-02-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; HE, Shuwen; DAI, Xing; LIU, Hong; LAI, Zhong; LONDON, Clare; XIAO, Dong; ZORN, Nicolas; NARGUND, Ravi; WO2013/33971; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, 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.179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, molecular formula is C12H9ClN2O3, molecular weight is 264.66, as common compound, the synthetic route is as follows.

2-chloro-4-nitro phenol 1Og (57.6 mmol, leq), 2-pycolyl chloride hydrogen chloride 9.45g (57.6 mmol, 1 equiv) cesium carbonate 41.3 (126.8 mmol, 2.2 equiv) and sodium iodide 8.64g (57.6 mmol, 1 equiv) were suspended in 200 mL acetonitrile. The reaction mixture was stirred at 60C for 5h. The resulted suspension was filtered and washed with 400 mL water, yielding 2-(2-chloro-4-nitro-phenoxymethyl)-pyridine (8g, 52%) as a red solid. 2-(2-chloro-4-nitro-phenoxymethyl)-pyridine (8 g, 30.2mmol, 1 equiv) and 8.44g iron (151.1 mmol, 5 equiv) were mixed in 100 mL acetic acid and 50 mL EtOAc and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52%) as a white solid. 1H-NMR (CDCl3) delta 5.18 (s, 2H), 6.50 (dd, IH), 6.76 (d, IH),. 6.80 (d, IH), 7.22 (m, IH), 7.64 (d, IH), 7.73 (td, IH), 8.55 (m, IH); LCMS RT = 0.89 min; [M+H]+ = 235.1.

Statistics shows that 179687-79-7 is playing an increasingly important role. we look forward to future research findings about 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; ZHANG, Chengzhi; WO2006/23843; (2006); A2;,
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.18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.name: 3-Methyl-2-nitropyridine

2-nitro 2-methylpyridine (4.2 g, 30.66 mmol) was dissolved in 100 mL of carbon tetrachloride,N-bromosuccinimide (5.5 g, 30.66 mmol) was added,Add the catalyst amount of the photoinitiator dibenzoyl peroxide, heat up to 100 C and reflux for 48 h.The reaction solution was returned to room temperature, the solvent was removed by distillation under reduced pressure, 50 mL of ice water was added,Extracted with ethyl acetate (40 mL X3). The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to a crude product. The crude product was purified by silica gel column chromatography (ethyl acetateEster: petroleum ether = 1: 10) 3-Bromoethyl-2-nitropyridine (2.9 g, 44.14%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-73-5, 3-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Jiao Tong University; Fu Lei; Xie Dongsheng; Qiao Yixue; Liu Wenlu; Yu Jihao; (24 pag.)CN106749045; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem