Tag: M.W:100-200

Electric Literature of 55676-22-7, 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. 55676-22-7, name is 3-Acetyl-6-chloropyridine. A new synthetic method of this compound is introduced below.

2 g (11.57 mmol) of 1-(6-chloropyrid-3-yl)ethanone and 70 mL of ammonium hydroxide are placed in a Parr reactor. The solution is heated at 130 C. overnight. The mixture obtained is evaporated to dryness, and the residue is taken up in ethyl acetate and washed with water and with saturated NaCl solution. The organic phase is dried over sodium sulfate and evaporated to dryness to give 1.14 g of 1-(6-aminopyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 137 tr (min)=0.35 1H NMR (300 MHz, delta in ppm, CDCl3): 2.41 (s, 3H), 6.45 (d, 1H), 6.88 (s, 2H), 7.86 (d, 1H), 8.58 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55676-22-7, 3-Acetyl-6-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; El-Ahmad, Youssef; Filoche-Romme, Bruno; Ganzhorm, Axel; Marciniak, Gilbert; Muzet, Nicolas; Ronan, Baptiste; Vivet, Bertrand; Zerr, Veronique; US2015/183804; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6602-32-0 , The common heterocyclic compound, 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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 stirred solution of 2-bromo-3-hydroxypyridine (50 g, 287.356 mmol) in THF at 0 C was added i-BuO-K (51.49 g, 459.7 mmol) portion wise. After stirring the reaction mixture for 15 mins, methoxymethyl chloride (34.473 mL, 459.77 mmol) was added to it at 0 C and the resulting reaction mixture was stirred for 12 h. at 25 C. Reaction mixture was diluted with water and extracted with ethyl acetate (4 x 500 mL). Organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford rude mass which was purified by column chromatography using silica gel (100-200 mesh) and 10% EtOAc-hexane as eluent to afford 2-bromo-3-methoxymethoxy-pyridine (45 g) as pale brown liquid. 1H-NMR (400 MHz, DMSO-d6): delta 8.03 (dd, ‘ = 4.5 Hz, J” = 1.3 Hz, 1H), 7.60 (dd, J’ = 8.1 Hz, J” = 1.1 Hz, 1H), 7.40 (dd, J’ = 8.2 Hz, J” = 4.5 Hz, 1H), 5.35 (s, 2H), 3.41 (s, 3H).

The synthetic route of 6602-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURADEV PHARMA PVT. LTD.; MIDDYA, Sandip; YADAV, Dharmendra B; SHRIVASTAVA, Ritesh; RAINA, Sushil; BANERJEE, Monali; SURYA, Arjun; (74 pag.)WO2016/27241; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1462-86-8, Adding some certain compound to certain chemical reactions, such as: 1462-86-8, name is 3-Aminopicolinic acid,molecular formula is C6H6N2O2, 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 1462-86-8.

General procedure: In a vial, 0.088 mmol (1.2 equiv) of the 3-aminopicolinic acid were added and dissolved in 0.5 mL mixture of DCM:DIEA (9:1), then 41 mg (0.110 mmol, 1.5 equiv) of HATU were added. The mixture was stirred for 10 min, and 20 mg (0.073 mmol, 1.0 equiv) N-(4-aminophenyl)phthalimide dissolved in 0.5 mL of DCM:DIEA (9:1), followed by 3 drops of DMF. The reaction was stirred for 24 h at room temperature. After this time, the reaction was quenched with the addition of water, and was worked up by extraction with DCM (2 mL, thrice). The organic phased was filtered through a phase separator, volatiles were evaporated, the crude was dissolved in DMSO and purified by preparative HPLC.

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. 1462-86-8, 3-Aminopicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gogliotti, Rocco D.; Engers, Darren W.; Garcia-Barrantes, Pedro M.; Panarese, Joseph D.; Gentry, Patrick R.; Blobaum, Anna L.; Morrison, Ryan D.; Daniels, J. Scott; Thompson, Analisa D.; Jones, Carrie K.; Conn, P. Jeffrey; Niswender, Colleen M.; Lindsley, Craig W.; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 12; (2016); p. 2915 – 2919;,
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

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

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

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: 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

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

Electric Literature of 133427-07-3 ,Some common heterocyclic compound, 133427-07-3, molecular formula is C9H8N2O2, 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 mixture of imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester (3.24 g, 18.3 mmol) and N-iodosuccinimide ( S) (4.11 g, 18.3 mmol) in acetonitrile (50 mL) is stirred at room temperature. After 2 hours, the reaction mixture is quenched with saturated aqueous Na2S2C>3 and extracted with EtOAc (3 x 100 mL). The combined organic layers are washed with water, brine, dried over Na2S04 and concentrated. The crude material is purified by silica gel chromatography eluting with 80% EtOAc in hexanes to afford 3-iodo-imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 99-110C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,133427-07-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem