Day: September 27, 2021

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. 1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4BrN3

A mixture of 6-bromo-1H-pyrazolo[4,3-b]pyridine (0.3 g, 2 mmol;)(Annova Chem Cat. No. L05238), (3,5-dimethoxyphenyl)boronic acid (0.33 g, 1.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (100 mg, 0.1 mmol), and potassium phosphate (0.64 g, 3.0 mmol) in 1,4-dioxane (1 mL) and water (0.12 mL) was degassed and sealed. It was stirred at 85 C. overnight. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.38 g). LCMS (M+H)+=256.2.

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, 1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine.

Reference:
Patent; Incyte Corporation; Zhuo, Jincong; Xu, Meizhong; Qian, Ding-Quan; US2014/171405; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 505084-59-3, 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.505084-59-3, name is 2-Chloro-5-(trifluoromethyl)nicotinic acid, molecular formula is C7H3ClF3NO2, molecular weight is 225.55, as common compound, the synthetic route is as follows.

To a stirred solution of 478 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (2 g, 8.87 mmol) in 45 THF (5 mL) and 139 MeOH (5 mL) was added 479 (trimethylsilyl)diazomethane (8.87 mL, 17.73 mmol) (2 M in 123 hexane) dropwise at -20 C. and the reaction was stirred at -20 C. for 2 h. The solvent was concentrated under reduced pressure and the residue was purified by flash silica gel chromatography to afford the 480 title compound as an oil. MS (ESI) m/z: 242.2 [M+H+]

The chemical industry reduces the impact on the environment during synthesis 505084-59-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76469-41-5, 2,3,5-Trifluoropyridine, 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 76469-41-5, blongs to pyridine-derivatives compound. Product Details of 76469-41-5

Example 1 Compound 1 4-(teri-butyldimethylsilyl)-2,3,5-trifluoropyridineA solution of diisopropylamine (98.85 g, 136.9 mL, 976.9 mmol) in THF (1.350 L) was cooled to -65C. n-BuLi (2.5 M in hexanes) (375.8 mL of 2.5 M, 939.4 mmol) was added dropwise via cannula over lh at such a rate as to maintain reaction temperature below -60C. Once the addition was complete the cooling bath was removed and the reaction mixture was allowed to warm up to 0C. The reaction mixture was stirred for 15 min at 0C, then re-cooled to -78C. 2,3,5-trifluoropyridine (100 g, 751.5 mmol) was added dropwise via cannula over 20 min at such a rate to maintain the reaction temperature below -69C. The reaction mixture was stirred for 45 min at -78C during which time the solution turned orange brown. A solution of tert-butyl- chloro-dimethyl-silane (147.2 g, 976.9 mmol) in THF (150 mL) was then added via cannula over 30 min. The reaction mixture was stirred at -78 C for 90 minutes during which time the solution darkened. Lc/Ms after this time indicated that the reaction was complete. A saturated ammonium chloride solution (300ml) was then added and mixture was allowed to warm up to RT. The reaction mixture was diluted with water (100 ml) and extracted with EtOAc (1.5L then 2 x 500ml). The combined organics were washed with saturated NaHCO (500ml) and brine (400 ml). The crude mixture was partially concentrated in vacuo, dried over magnesium sulfate, filtered and concentrated in vacuo to an oil. The crude was purified by flash chromatography (CombiFlash Companion XL, 1.5kg column, 0-20% ethyl acetate in petroleum ether). This afforded the title compound as a colourless oil (136.2 g, 73%); XH NMR (CDC13) 0.34 (6H, s), 0.89 (9H, s), 7.73 (1H, s); MS ES(+) 248.25 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76469-41-5, 2,3,5-Trifluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; GOLEC, Julian, M.C.; SETTIMO, Luca; FRAYSSE, Damien; BRENCHLEY, Guy; BOYALL, Dean; TWIN, Heather; YOUNG, Stephen; MILLER, Andrew, W.; DAVIS, Christopher, John; WO2011/94283; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13600-49-2 ,Some common heterocyclic compound, 13600-49-2, molecular formula is C8H5F3N2, 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.

A. tert-Butyl ((6-Methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)carbamate 6-Methyl-4-(trifluoromethyl)nicotinonitrile (1.0 equiv.) was dissolved in MeOH (0.1 M), wet Raney nickel was added, followed by ammonium hydroxide (32 equiv.). The reaction vessel was evacuated three times, refilled with hydrogen and then equipped with a hydrogen balloon and stirred at room temperature for 48 h. The mixture was filtered through a short pad of celite which was washed with MeOH. Ethanol was added to remove excess water upon concentration. The volatile solvents were removed to afford crude product which was dissolved in DCM. DIEA (1.8 equiv.) was added followed by BOC2O (0.95 equiv.). The reaction was stirred at room temperature for 1 h. The volatile solvent was removed and the residue was purified via Biotage chromatography (10-100% ethyl acetate in hexanes) to afford tert-butyl ((6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)carbamate (90% yield); MS(ESI) m/z 290.3 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13600-49-2, its application will become more common.

Reference:
Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 871826-12-9, (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride, 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, 871826-12-9, blongs to pyridine-derivatives compound. name: (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride

General procedure: The carboxylic acid 8 is dissolved in DMF and 2 eq. of the corresponding amine component, 1.5 eq. of HATU and 3 eq. of triethylamine are added. The reaction mixture is stirred at rt until TLC and/or LCMS indicate complete consumption of the starting material (2 h), then water is added. The formed precipitate is filtered off, washed with water and dried in a vacuum drying cabinet at 40C. If appropriate, the product is purified by preparative HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,871826-12-9, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; PANKNIN, Olaf; BAeURLE, Stefan; RING, Sven; SCHWEDE, Wolfgang; BONE, Wilhelm; NOWAK-REPPEL, Katrin; BENDER, Eckhard; NUBBEMEYER, Reinhard; GNOTH, Mark, Jean; WO2013/107743; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14338-32-0, 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. 14338-32-0, name is 2-Chloro-1-methylpyridinium iodide, molecular formula is C6H7ClIN, 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.

Step F: 2-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3*30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2*50 cm3), brine (1*50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluding with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H) +522.3.

According to the analysis of related databases, 14338-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dolle, Roland E.; Tuthill, Paul Anson; US2004/209857; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5409-39-2, 5-Chloro-3-nitropyridin-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, 5409-39-2, blongs to pyridine-derivatives compound. Formula: C5H4ClN3O2

To a solution of intermediate 32a (10.0 g, 57.6 mmol) in HBr [(31 .0 mL (100%), 286.4 mmol)] at 0 00 sodium nitrite (13.8 g, 199.9 mmol) was added drop wise. To the stirred solution Br2 (10.0 mL, 197.1 mmol) was added in water and stirred at room temperature for 1 h. The reaction mixture was basified with NaHCO3 solution (pH=7) and extracted with ethyl acetate, washed with water, and dried over anhydrousNa2SO4 The solvent was removed under vacuo to yield the title product (10.0 g,73.0%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5409-39-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-86-4 ,Some common heterocyclic compound, 58584-86-4, molecular formula is C8H7Cl2NO2, 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.

The first step of Scheme 5: A dry round bottom flask was charged with NaH (264 mg of a 60% dispersion in mineral oil, 6.6 mmole) and the reagent washed twice with hexane. 5 mL dry DMF was added and benzyl alcohol (0.62 mL, 6.0 mmole) was added dropwise. After H2 evolution had ceased the reaction mixture was added dropwise to a 0 C. solution (10 mL) of 2,6-dichloro-nicotinic acid ethyl ester (1.33 g, 6.0 mmole). It was stirred 15 minutes, and then allowed to stir another 20 minutes at room temperature. The reaction mixture was then poured into 150 mL water and extracted with ether (3×75 mL). Combined organic phases were washed with water, brine and dried over MgSO4. Filtration and evaporation gave the crude product which was then purified by chromatography on silica gel using a gradient of hexane/EtOAc (0 to 4%) as eluent. Pure fractions were combined and evaporated to give 818 mg (47%) of a 1:1 mixture of 2-benzyloxy-6-chloro-nicotinic acid ethyl ester and 6-benzyloxy-2-chloro-nicotinic acid ethyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-86-4, its application will become more common.

Reference:
Patent; Lee, Jinbo; Kirincich, Steve J.; Smith, Michael J.; Wilson, Douglas P.; Follows, Bruce C.; Wan, Zhao-Kui; Joseph-McCarthy, Diane M.; Erbe, David V.; Zhang, Yan-Ling; Xu, Weixin; Tam, Steve Y.; US2005/203081; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 82257-09-8, name is 3-Bromo-4-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of Compound 4 (150 mg, 414.11 mumol, 1 eq), 3-bromo-4-methoxy-pyridine (77.86 mg, 414.11 mumol, 1 eq), Pd(PPh3)2Cl2 (29.07 mg, 41.41 mumol, 0.1 eq), Na2CO3 (87.78 mg, 828.21 mumol, 2 eq) in dioxane/H2O (10 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 110 C. for 3 hr under N2 atmosphere. The reaction mixture was diluted with H2O (20 mL), then the mixture was extracted with EA (20 mL*3). The combined organic layers were washed with brine (20 mL*2), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Silica gel, Petroleum ether/Ethyl acetate=0:1). Then the residue was purified by prep-HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water (10 mM NH4HCO3)-ACN]; B %: 24%-54%, 10 min). Example 55 (23 mg, 63.63 mumol, 15% yield, 95% purity) was obtained as a light yellow solid. 1H NMR (400 MHz, CDCl3) delta=1.33-1.44 (m, 1H), 1.91-2.13 (m, 2H), 3.94 (s, 3H), 4.79-5.05 (m, 1H), 6.96 (d, J=5.87 Hz, 1H), 7.63 (dd, J=8.38, 1.65 Hz, 1H), 7.87 (d, J=8.44 Hz, 1H), 8.02 (d, J=1.47 Hz, 1H), 8.51-8.55 (m, 2H), 10.35 (br s, 1H); LCMS (electrospray) m/z 344.3 (M+H)+.

The synthetic route of 82257-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 1ST Biotherapeutics, Inc.; LEE, Jinhwa; KIM, Jae Eun; JO, Suyeon; LEE, Gwibin; LIM, Keonseung; PARK, A Yeong; KIM, Misoon; JUNG, Gyooseung; LIM, Seung Mook; LEE, Minwoo; YANG, Heekyoung; KIM, Hyonam; KIM, Hyeongjun; LI, Wanjun; FAN, Mingzhu; (82 pag.)US2019/100500; (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. 52568-28-2, name is 2-(Pyridin-2-yl)propan-2-amine, molecular formula is C8H12N2, 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-(Pyridin-2-yl)propan-2-amine

General procedure: To a solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel to give the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 52568-28-2.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem