Day: March 16, 2021

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.164666-68-6, name is 6-Chloro-2-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Application In Synthesis of 6-Chloro-2-methylpyridin-3-amine

To an ice cold solution of 6-chloro-2-methylpyridin-3-amine (12 g, 84 mmol) and AcOH (5.1 g, 84 mmol) in MeOH (198 g, 250 mL) was dropwise added bromine (13.5 g, 84 mmol). The resulting solution was stirred at ice bath temperature overnight after which it was concentrated under vacuo. The obtained residue was dissolved in EtOAc and sequentially washed with saturated aqueous NaHCO3 solution, 10% Na2S2O3 aqueous solution, brine and dried (Na2SO4). The solvent was removed under vacuo and the obtained crude material was purified by flash chromatography to afford 4-bromo-6-chloro-2-methylpyridin-3-amine (12.6 g). 1H NMR (500 MHz, Chloroform-d) delta 7.30 (s, 1H), 4.04 (brs, 2H), 2.46 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,164666-68-6, 6-Chloro-2-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; US2019/185489; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 106877-33-2, Adding some certain compound to certain chemical reactions, such as: 106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine,molecular formula is C6H5F3N2, 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 106877-33-2.

[0372] A stirred solution of 7-bromo-6-methylquinoline Int-1 (Example 86) (150 mg, 0.675 mmol), 6-(trifluoromethyl)pyridin-3-amine (131 mg, 0.810 mmol) and Na2CC>3 (142 mg, 1.351 mmol) in acetonitrile (5 mL) was degassed with Argon in a microwave vessel for 15 min. Then Mo(CO)6 (178 mg, 0.675 mmol), 3RhoEtaBetaEpsilon4 (19.6 mg, 0.0675 mmol) and Pd(OAc)2 (15.1 mg, 0.0675 mmol) were added, and degassing was continued for additional 10 min. Then the reaction mixture was irradiated in microwave at 90 C for 3 hrs. After completion (checked by TLC), the reaction mixture was diluted with water (20 mL) and extracted with Ethyl Acetate (2×50 mL). Combined organic layer was washed with water (2×20 mL), brine (20 mL) and dried over anhydrous sodium sulfate. The organic layer was evaporated under reduced pressure to afford crude product. The crude compound was purified by Grace (reverse phase) column chromatography using 0.05 % HCOOH in CCN as eluent to afford 50 mg (21% yield) of the desired compound 160 as an off- white solid. MS (ESI) m/z: 332.21 [M+H]+. 1H NMR (DMSO-i/6, 400 MHz): delta 11.18 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.94 (dd, J = 4.4, 2.0 Hz, 1H), 8.50 (dd, J = 8.0, 1.6 Hz, 1H), 8.35 (dd, J Hz, 1H), 8.24 (s, 1H), 7 ‘.95-7 ‘.92 (m, 2H), 7.60 (dd, J= 8.4, 4.0 Hz, 1H), 2.61 (s, 3H).

According to the analysis of related databases, 106877-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); 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. 175422-04-5, name is 2,6-Dibromo-4-nitropyridine. A new synthetic method of this compound is introduced below., COA of Formula: C5H2Br2N2O2

Methanesulfinic acid sodium salt (1.66 g, 16.3 mmol) is added to a solution of 2,6- dibromo-4-nitropyridine (0.917 g, 3.253 mmol) and DMF (15 ml_). After 1 h the DMF is removed in vacuo and the residue is taken up in CH2CI2 (150 ml.) and brine (150 ml_). The layers are mixed and then separated. The aqueous layer is extracted further with CH2CI2 (2 x 150 ml_). The combined organic layers are then dried (Na2SO4), filtered and concentrated. The residue is then separated via flash chromatography (SiO2, 5-30% EtOAc/heptane gradient) to give the title compound 2,6-dibromo-4-methanesulfonylpyridine as a white powder. MS (ESI) m/z 316.2 (M+1 ). 1H NMR (400 MHz, CDCI3) delta ppm 7.94 (s, 2 H), 3.12 (s, 3 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, 175422-04-5, 2,6-Dibromo-4-nitropyridine.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-14-1, 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 884495-14-1, name is 5-Bromo-2-methoxy-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromo-2-methoxy-4-methyl-3-nitro-pyridine (2.0 g, 8.1 mmol), bis(pinacolato)diboron (10.28 g, 40.48 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.19 g, 1.62 mmol) and potassium acetate (2.38 g, 24.29 mmol) in 1,4-dioxane (40 mL) was stirred at 100 C. for 2 hours. The mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with petroleum ether/ethyl acetate (1/1) to afford 2-methoxy-4-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.1 g, 7.14 mmol) as a yellow solid. LCMS (ESI) [M+H]+=295.

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 884495-14-1, 5-Bromo-2-methoxy-4-methyl-3-nitropyridine.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16063-70-0, Adding some certain compound to certain chemical reactions, such as: 16063-70-0, name is 2,3,5-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 16063-70-0.

To 30.74 g of potassium tert-butoxide in 100 ml of dimethylsulfoxide, 16.72 g of nitromethane was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. Then, the reaction mixture was cooled with ice again, and to the reaction mixture, 25.00 g of 2,3,5-trichloropyridine in 100 ml of dimethylsulfoxide was added dropwise with stirring, and after the addition, the mixture was stirred at 70 C. for another 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 200 ml of 10% aqueous hydrochloric acid with stirring under cooling with ice and extracted with ethyl acetate (200 ml¡Á1). The resulting organic layer was washed with water (100 ml¡Á1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 10:90) as the eluent to obtain 10.10 g of the desired product as a pale yellow oil

According to the analysis of related databases, 16063-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; Iwasa, Motoyoshi; Tomizawa, Mitsutaka; Tsuji, Keisuke; Nakamura, Toshiyuki; Mita, Takeshi; Kuwahara, Hidehito; asahi, Miho; Imanaka, Hotaka; (342 pag.)JP2016/11286; (2016); A;,
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. 757978-18-0, name is 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H4BrIN2

Step 1: Synthesis of 5-bromo-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 2.30 g (11.67 mmol) of 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine was dissolved in 90 ml of anhydrous THF under nitrogen. An excess of sodium hydride was added at room temperature and subsequently 3 ml of tri-iso-propylsilyl chloride were added. The reaction mixture was allowed to stir at ambient temperature for 4 h. The mixture was distributed between ethyl acetate and a saturated aqueous solution of ammonium chloride. The aqueous phase was extracted three times with ethyl acetate and the organic phases were combined, washed with brine, dried over sodium sulfate and evaporated. The crude material was purified by flash chromatorgraphy on silica gel using a gradient of ethyl acetate in hexanes to afford 3.493 g (7.235 mmol, 62% yield) of -bromo-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine as a crystalline solid. 1H-NMR (d6-DMSO): (58.34 (d, J=1.9 Hz, 1H), 7.88 (d, J=2.0 Hz, 1H), 7.72 (s, 1H), 1.86 (m, 3H), 1.05 (d, J=7.8 Hz, 18H).

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, 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2006/30583; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26218-75-7, 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 26218-75-7, name is Methyl 6-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2-carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain crude 2-(6-bromo-2-pyridinyl)-2-propanol as a yellow oily substance. 1H-NMR (400 MHz, CDCl3) delta: 7.56 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, dd, J=7.8, 1.0 Hz), 1.55 (6H, s). ESI-MS Found: m/z[M+H]+ 216, 218.

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 26218-75-7, Methyl 6-bromopicolinate.

Reference:
Patent; Merck Sharp & Dohme Corp.; Shumway, Stuart Denham; (37 pag.)US2016/8361; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74420-00-1, 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 74420-00-1, name is 4-Amino-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 100 mg (321 pmol) 6-bromo-8-methyl-2H-spiro[cyclohexane-1 3- imidazo[1,5-a]pyridine]-1,5-dione (GAS-No: 1849592-70-6; PGT Int. AppI. (2015), WO 2015200481) and 47 mg (353 pmol) 1 H-pyrrolo[2,3-b]pyridin-4-amine (GAS-No: 74420-00-1) in 12 mL 1 ,4-dioxane was added 314 mg cesium carbonate and the mixture was degassed and purged with argon several times. 20 mg 4,5-bis(diphenylphosphino)-9,9-dim ethylxanthene, 16 mg 2-(dicyclohexyl-phosphino)-2,4,6-triisopropylbiphenyl, 7.7 mg palladium(ll)acetate and 31 mg tris(dibenzylideneacetone)dipalladium(0) were added and the mixture was stirred at 1000 for 2 hours. The mixtu re was concentrated and the residue purified by flash chromatography (Biotage SNAP cartridge NH 28 g,methanol :dichloromethane) followed by preparative TLC (methanol :dichloromethane) to give 8 mg (7%) of the title compound.LC-MS: m/z = 364.5 [M¡ÂH].1HNMR (400 MHz, DMSO-d6), 6 [ppm]= 1 .24 (1 H), 1 .48 (2H), 1 .57-1 .80 (5H), 2.43 (3H),3.03 (2H), 6.48 (1 H), 7.06 (1 H), 7.21 (1 H), 7.35 (1 H), 8.09 (1 H), 8.20 (1 H), 10.04 (1 H), 11.62 (1H).

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 74420-00-1, 4-Amino-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 105752-11-2, 3-Amino-4-iodopyridine, 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, Application In Synthesis of 3-Amino-4-iodopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Amino-4-iodopyridine

To a stirred solution of 4-iodopyridin-3-amine (500 mg, 2.2 mmol) in acetonitrile (5 mL) wasadded tert-butyl (2-amino-2-thioethoxyethyl)carbamate (561 mg, 2.9 mmol) and CaO (255 mg,4.5 mmol) at room temperature. The reaction mixture was purged with argon for 15 minutes,then dppf (151 mg, 0.27 mmol) and Pd2(dba)3 (64 mg, 0.06 mmol) was added to the reactionmixture. The reaction mixture was purged with argon for further 5 minutes and stirred in sealedtube at 60 C for 16 h. The reaction mixture was filtered through celite pad and washed the pad

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ANTABIO SAS; LEIRIS, Simon; DAVIES, David Thomas; EVERETT, Martin; SPRYNSKI, Nicolas; SUTTON, Jonathan Mark; BODNARCHUK, Michael Steven; PALLIN, Thomas David; CRIDLAND, Andrew Peter; BLENCH, Toby Jonathan; CLARK, David Edward; ELLIOTT, Richard Leonard; (197 pag.)WO2018/172423; (2018); 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.30766-22-4, name is Methyl 5-hydroxynicotinate, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.Safety of Methyl 5-hydroxynicotinate

Example V Preparation of [(5-methoxy-6-chloropyridin-3-yl)methyl](methyl)-oxido-lambda4-sulfanylidenecyanamide (5) To a flask containing methyl-5-hydroxynicotinate (4.5 g, 29 mmol) was added sodium hypochlorite aqueous solution (6.15%, 26.7 mL, 22 mmol) dropwise under ice bath cooling. After 30 min of stirring, 2 M HCl (20 mL) was added and the resulting white crystals collected by filtration to give 2.31 g of 6-chloro-5-hydroxynicotinic acid methyl ester in 42% yield. 1H NMR (400 MHz, CDCl3) delta 10.32 (bs, 1H), 8.48 (d, 1H), 7.84 (d, 1H), 7.40 (s, 1H), 3.93 (s. 3H); LC-MS (ELSD): mass calcd for C7H6ClNO3 [M]+ 187. Found 187.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,30766-22-4, Methyl 5-hydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Zhu, Yuanming; Loso, Michael R.; Nugent, Benjamin M.; Huang, Jim X.; Rogers, Richard B.; US2008/108667; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem