Day: August 9, 2021

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

a) (5-Bromo-2-chloro-pyridin-3-yl)-methyl-amine A solution of 5-bromo-2-chloro-pyridin-3-ylamine (CAS registry 588729-99-1) (565 mg, 2.72 mmol) in THF (4 ml) at 0 C. was treated with BuLi 1.6M in hexane (0.17 ml, 0.17 mmol), the resulting mixture was stirred at 0 C. for 0.5 h, then methyl iodide (0.17 ml, 2.72 mmol) was slowly added. The reaction mixture was allowed to warm to rt and was stirred for 18 h. The orange/brown mixture was poured into sat. aq. NaHCO3 soln., and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and purified by flash chromatography on silica gel (cyclohexane/EtOAc 95:5 to 60:40) to afford the title compound as an orange solid (354 mg, 59% yield). HPLC RtM1=0.94 min; ESIMS: 221, 223, 225 [(M+H)+]. 1H NMR (400 MHz, DMSO-d6): delta 7.65 (d, 1H), 7.14 (d, 1H), 6.11 (d, 1H), 2.74 (d, 3H).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75711-00-1, 2-Chloro-3-methoxy-5-nitropyridine, 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, 75711-00-1, blongs to pyridine-derivatives compound. Formula: C6H5ClN2O3

Step 3 2-Chloro-3-methoxy-5-nitropyridine (400 mg, 2.12 mmol), pyrrolidine (0.21 mL, 2.55 mmol), potassium carbonate (880 mg, 6.38 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (80 mg) was dissolved in acetonitrile. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and then was concentrated under reduced pressure. Then the mixture was extracted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give 3-methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridine (458 mg, 97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75711-00-1, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6635-90-1, 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 6635-90-1, name is 2-Methoxy-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-methoxy-4-methyl-5-nitropyridine (4.30 g, 25.57 mmol) and dimethylformamide dimethylacetal (35 ml) was heated at reflux under nitrogen for 40 hours. Ethyl acetate was added to this solution (150 ml), and this mixture was washed with water (150 ml). The aqueous extract was back-extracted with ethyl acetate (100 ml), and the organic extracts were combined, dried (Na2 O4), and evaporated under reduced pressure to yield a purple solid. The solid was dissolved in absolute ethanol (200 ml), and 5% palladium on carbon (3.0 g) was added to this solution which was shaken under a hydrogen atmosphere (3 atm) for 3 hours. The resultant reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. Flash chromatography of the residue yielded compound 9 (2.05 g, 13.84 mmol, 54% last step, 50% overall) as a white crystalline solid: mp, 123-124 C.; IR (KBr) 1625, 1580, 1490, 1460, 1320, 1150 cm-1; 1 H NMR (DMSO-d6) delta 11.28 (br s, 1H), 8.37 (s, 1H), 7.57 (t, J=2.8 Hz, 1H), 6.86 (s, 1H), 6.33 (br m, 1H), 3.82 (s, 3H); 13 C NMR (DMSO-d6) delta 157.2, 136.4, 131.5, 130.7, 130.0, 99.6, 96.8, 53.4; LRMS (m/z, relative intensity) 149 (20), 148 (M+, 98), 147 (100), 119 (46), 118 (79), 117 (26), 105 (31), 91 (15), 70 (16); HRMS calculated for C8 H8 N2 O:148.0657, found: 148.0613.

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 6635-90-1, 2-Methoxy-4-methyl-5-nitropyridine.

Reference:
Patent; Pfizer Inc.; US5051412; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61338-13-4, 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 61338-13-4, name is 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Stirring blade,In a 1 L three-necked flask equipped with a thermometer, 60 g (201.8 mmol) of the pyridine carboxylic acid compound was suspended in 270 mL of tetrahydrofuran,It was cooled to 10 C.Under nitrogen flow70% sodium bis (2-methoxyethoxy) aluminum hydrideOf a toluene solution240 g (706.2 mmol) was added dropwise,The reaction was carried out at 40 C. for 5 hours.After completion of the reaction,The reaction solution was cooled to 10 C.,The reaction solution was added to 275 mL of a 35% by mass Rochelle salt aqueous solution cooled to 10 C. with stirring for 5 minutes.The temperature of the mixed solution at this time was 15 C.In addition, precipitation of aluminum hydroxide was not confirmed.Thereafter, the mixture was stirred for 10 minutes, and an organic layer and an aqueous layer were separated.The organic layer was concentrated under reduced pressure to obtain a pyridine methanol compound as a residue.240 mL of diethyl ether was added to the residue, and the mixture was stirred at room temperature for 30 minutes to obtain a crystallized pyridine methanol compound.After filtering the crystals,Dried under reduced pressure at 40 C. for 5 hours,Pyridine methanol compound (51 g).(Yield 89%, purity 99.3%, excess reductant amount 0.2%).

According to the analysis of related databases, 61338-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; KASAI, SOKO; MIYAOKU, TAKAYUKI; (10 pag.)JP2017/154976; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33252-64-1, 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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

3-Nitro-5-(trifluoromethyl)pyridin-2-ol (31.00 g, 149 mmol) was dissolved in acetonitrile (250 ml) to give a dark brown solution. Phosphorus(V) oxybromide (85 g, 298 mmol) was added and the mixture was heated at reflux for 4 hours and then stirred at RT overnight. The reaction mixture was quenched by pouring into vigorously stirring water (600 ml) containing sodium hydrogencarbonate (1 10 g). The dark brown mixture was extracted with DCM (3 x 200 ml) and the organic phase was washed with water (200 ml) and brine (100ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a brown oil. H-NMR: [400MHz, CDCI3, ? 8.87 (1 H, d, J = 1.4Hz, ArH), 8.39 (1 H, d, J = 1 .9Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38373; (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. 1121-76-2, name is 4-Chloropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Chloropyridine 1-oxide

4-Chloropyridine-N-oxide (3.0 g, 23 mmol), 4-trifluoromethylphenylboronic acid (6.57 g, 34.6 mmol), K2CO3 (4.8 g, 35 mmol) and PdCl2(dppf) (470 mg, 0.57 mmol) were stirred in DMSO (40 mL) under vacuum for 30 min. The flask was flushed with nitrogen, and the mixture was heated to 80 C. for 10 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5*), dried, concentrated, and the residue was purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (1.90 g, 34%) as a tan solid: ESI MS m/z 240 [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, 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 144100-07-2 ,Some common heterocyclic compound, 144100-07-2, molecular formula is C5H3BrFN, 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 2-bromo-6-fluoropyridine (212 mg, 1.21 mmol), (R)-1-(tetrahydro-2H- pyran-4-yl)ethanamine (200 mg, 1.21 mmol), DIPEA (187 mg, 1.45 mmol) and DMSO (3 ml_) was heated in a sealed tube at 90 °C for 18 hrs. The reaction mixture was allowed to cool to room temperature, poured into water (30 ml_) and stirred for 20 min. The mixture was extracted with EtOAc (3x 15 ml_). The combined organic layers were washed with brine (100 ml_) and concentrated to dryness under reduced pressure. The residue was purified by column chromatography [silica gel] providing (R)-6-bromo-N-(1- (tetrahydro-2H-pyran-4-yl)ethyl)pyridin-2-amine (290 mg). LCMS (m/z): 285.0/286.9 [M+H]+; Rt = 0.91 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144100-07-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; NG, Simon C.; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2012/101063; (2012); 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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-3-(trifluoromethyl)pyridine

To a solution of 5.37 g (32.8 mmol) of 3-trifluoromethyl-pyridin-2-ylamine (Fluorochem Ltd., Derbyshire, United Kingdom) in 100 ml of dry CH3CN, 6.45 g of NBS are added in 4 equal portions over a period of 1 h at 0-50C under argon. The cooling bath is removed and stirring is continued for 3 h. The solvent is evaporated under vacuum, the residue is dissolved in EtOAc and washed with water and brine. The organic phase is dried over Na2SO4 and evaporated. The title compound is a red-dish-yellow oil which is used after drying in the dark for 5 h at RT and under high vacuum in the next step without further purification. ES-MS (M+1 ): = 239; 241 ; HPLC: tR = 5.501 min. Example 1.4 1 -(2-Methoxy-pyridin-3-yl)-3-methyl-8-(6-methylamino-pyridin-3-yl)-1 ,3-dihydro- imidazo[4,5-c]quinolin-2-one

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, 183610-70-0, 2-Amino-3-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 552331-00-7, 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. 552331-00-7, name is 4-Iodopyridin-2-amine. A new synthetic method of this compound is introduced below.

Reference Example 42; 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-oneTo a solution of 4-iodopyridin-2-amine (2.0 g, 9.09 mmol), 5-phenyl-1,3-oxazolidin-2-one (1.7 g, 10.5 mmol) obtained in Reference Example 41 and potassium carbonate (2.5 g, 18.2 mmol) in 1,4-dioxane (30 mL) were added copper iodide (173 mg, 909 mumol) and N,N’-dimethylethylenediamine (80 mg, 909 mumol) at room temperature, and the mixture was heated under reflux for 16 hr under an argon stream. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.78 g, yield 77%) as crystals.melting point 155-156 C. (ethyl acetate-hexane)1H-NMR (CDCl3) delta: 3.90 (1H, dd, J=9.0, 7.5 Hz), 4.35 (1H, t, J=9.0 Hz), 4.49 (2H, br s), 5.64 (1H, t, J=7.5 Hz), 6.67 (1H, dd, J=6.0, 2.1 Hz), 6.93 (1H, d, J=2.1 Hz), 7.34-7.50 (5H, m), 8.00 (1H, d, J=6.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,552331-00-7, 4-Iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 917023-06-4, 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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below.

A single-necked round-bottomed flask was charged with Compound 2 (1.80g, 7.82mmol), 3-fluorobenzylamine (2.94g, 23.5mmol), and anhydrous anisole 05g). The reaction was stirred at 150C until reaction was complete LCMS (~23h) and then allowed to cool to near RT. Crystals of the desired product, Compound 3, formed during the cooling process and were collected by filtration and washed with toluene. Compound 3 was obtained as colorless crystalline solid (1.59g, 63% yield) and characterized by 1H NMR (400MHz, DMSO-d6): 3 ,69 (s, 2H), 4,30 (d, 2H), 7.0-7.15 (m, 3H), 7.3-7.4 (m, 2H), 7.99 (dd, 1H), 8.61 (fine d, 1H), 8.66 (br t, 1H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; ATHENEX, INC.; SMOLINSKI, Michael P.; NASIEF ABDEL-SAYED, Nader N.; HANGAUER, JR., David G.; (197 pag.)WO2018/31988; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem