Category: pyridine-derivatives

Application of 75358-90-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 75358-90-6 as follows.

To a nitrogen flushed solution of Description 34 (14.27 g, 81 mmol) and conc. HC1 (15 ml) was added 10% Palladium on carbon (2 g), and the resulting mixture hydrogenated at 50 psi until HPLC and MS indicated complete conversion (approx 2 days). The catalyst was removed by filtration and the filtrate evaporated to give the title compound (17.55 g, 100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75358-90-6, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C, followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over MgS04 and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,197376-47-9, Ethyl 6-Chloropyridine-3-acetate, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77555-27-2, 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. 77555-27-2, name is 2-(Pyridin-2-ylthio)ethanol. A new synthetic method of this compound is introduced below.

A solution of 0.2 g (0.55 mmol) of the product from example 11, Step C and 0.1 g (0.66 mmol) of the product from Example 23, step A in toluene (20 ml) was refluxed for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The combined organic layers were successively washed with water (25 ml x 2) and brine (25 ml x 2), dried over anhydrous sodium sulphate and evaporated under vacuo. The solid residue was purified by column chromatography over silica gel using 60 % ethyl acetate in hexane as the eluent to afford 0.1 g of the title compound as a yellow solid. ¹H NMR (400 MHz, DMSOd6) 8 3 – 3.11 (2H, t), 3.28 (2H, t), 3.55 – 3.56 (4H, t), 3.72 – 3.75 (4H, t), 6.92 – 6.95 (1H, d), 7.11 – 7.14 (1H, d), 7.35 – 7.37 (1H, d), 7.51 – 7.59 (3H, m), 7.62 – 7.67 (2H, m), 7.99 – 8.03 (3H, m), 8.08 – 8.14 (1H, m), 8.43 – 8.45 (1H, d), 9.08 – 9.13 (1H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77555-27-2, its application will become more common.

Reference:
Patent; TORRENT PHARMACEUTICALS LTD; WO2005/97746; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19235-89-3 ,Some common heterocyclic compound, 19235-89-3, molecular formula is C6H3ClN2, 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 teflon capped vial was charged with 4-amino-3- fluorophenol (0.291 g, 2.29 mmol) and anhydrous DMF (2.3 mL). The resultant solution was de-gassed in vacuo and backfilled with argon (3x). The vial was treated with sodium te/ -butoxide (0.27 g, 2.41 mmol) under argon and quickly capped. The reaction mixture was stirred at RT for lh. After addition of 4-chloropicolinonitrile (0.317 g, 2.29 mmol) and K2CO3 (0.174 g, 1.26 mmol), the vial was de-gassed again and heated in a 90 C oil bath overnight. The reaction mixture was diluted with EtOAc (60 mL) and washed with brine (25 mL). The aqueous phase was back-extracted with EtOAc (50 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO^, concentrated in vacuo and purified by chromatography to afford 4-(4-amino-3- fluorophenoxy)picolinonitrile (0.162 g, 31% yield) as a colorless oil. FontWeight=”Bold” FontSize=”10″ H NMR (DMSO- d6) delta 8.56 (d, J = 5.6 Hz, 1H), 7.62 (d, J = 2.0 Hz, 1H), 7.14 (dd, J = 6.0 , 2.8 Hz, 1H), 7.03 (dd, J = 1 1.6, 2.4 Hz, 1H), 6.88-6.77 (m, 2H), 5.25 (s, 2H); MS (ESI) m z: 230.0 (M+H+).

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. 19235-89-3, 4-Chloropyridine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; PETILLO, Peter A.; KAUFMAN, Michael D.; WO2013/36232; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3, 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. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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.

A mixture of impure 5-(4-ethylpiperazin- 1 -yl)pyridin-2-amine (1.00 g, 4.85′ mmol assumed), 8-bromo-6-chloroimidazo[l ,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-l,r-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1 : 1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1 : 19 methanol/methylene chloride to 1 :6methanol/methylene chloride) to afford 6-chloro-Ar-(5-(4-ethylpiperazin-l-yl)pyiidin-2- yl)imidazo[l,2-a]pyridin-8-amine as a yellow-green solid: NMR (400 MHz, DMS0- )d 9.12 (s, 1H), 8.30 (d, J = 2.0 Hz, 1H), 8.26 (d, J = 2.0 Hz, 1H), 7.99 (d, J = 2.8 Hz, 1 H), 7.89 (d, J = 0.8 Hz, 1H), 7.55 (d, J= 0.8 Hz, 1H), 7.43 (dd, J = 8.8, 2.8 Hz, 1H), 7.35 (d, J= 8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1097839-70-7, Adding some certain compound to certain chemical reactions, such as: 1097839-70-7, name is 5-Methoxy-2-methyl-1H-pyrrolo[2,3-c]pyridine,molecular formula is C9H10N2O, 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 1097839-70-7.

A solution of 5-methoxy-2-methyl-lH-pyrtauolo[2,3-c]pyridine (530mg, 3.3mmol), Cs2CO3 (3eq) and methyl (2R)-2-[3-(bromomethyl)-4-chlorophenoxy]propanoate (1.2eq) in DMF (2OmL) was stirred at 25 C for 8 hours. The reaction mixture was diluted with EtOAc, washed with water (2x) and satd NH4Cl (Ix). The organic layer was dried over Na2SO4 and concentrated. Purification via flash chromatography eluding with a gradient of 0 to 100% EtOAc/hexanes provided methyl (2R)-2-{4-chloro-3-[(5-methoxy-2-methyl-lH-pyrrolo[2,3- c]pyridin-l-yl)methyl]phenoxy}propanoate as a yellow syrup.1H NMR (500 MHz, CDCl3): delta 8.02 (s, IH), 7.25 (d, IH), 6.82 (s, IH), 6.68 (dd, IH), 6.25 (s, IH), 5.76 (d, IH), 5.26 (s, 2H), 4.36 (q, IH), 3.91 (s, 3H), 3.54 (s, 3H), 2.31 (s, 3H), 1.42 (d, 3H).

According to the analysis of related databases, 1097839-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/5672; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 727356-19-6, 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 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-((6-Bromopyridin-2-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H- imidazo[2,1-b][1 ,3,6]oxadiazocine (7.2.18)A solution of 2-bromo-6-(chloromethyl)pyridine (1 .0 g, 5.05 mmol) in acetone (50 ml) was treated with sodium iodide (3.8 g, 25.2 mmol). The mixture was refluxed for an hour, potassium carbonate (4.2 g, 30.3 mmol) was added to the reaction. 9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1 – b][1 ,3,6]oxadiazocine, 7.1.3 (1 g, 5.05 mmol) was dissolved in acetone and added to the mixture and stirred overnight. The reaction mixture was filtered and evaporated. The crude was dissolved in a mixture of ethyl acetate and methanol (95%:5%) and filtered through a pad of silica. The silica was washed a few times with the ethyl acetate and methanol mixture. The washings were combined and the solvent evaporated to yield 4-((6- bromopyridin-2-yl)methyl)-9-nitro-3,4,5,6-tetrahydro-2H-imidazo[2,1 – b][1 ,3,6]oxadiazocine (1 .7 g, 4.6 mmol, 92 %) with 68 % purity. The sample was further purified using prep HPLC. See Table 19 for analytical data.

According to the analysis of related databases, 727356-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ITHEMBA PHARMACEUTICALS (PROPRIETARY) LIMITED; MUSONDA, Chitalu, Christopher; EDLIN, Christopher, David; BOYLE, Grant, Alexander; WO2013/72903; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 936342-91-5, Adding some certain compound to certain chemical reactions, such as: 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride,molecular formula is C6H6BrCl2N, 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 936342-91-5.

5-bromo-2-chloromethyl-pyridine (243mg, 2mmol) and N- isobutyryl piperazine (289mg, 3mmol) was dissolved in the N, N- dimethylformamide (10ml), followed by addition of potassium carbonate ( 691mg, 10mmol), stirred at room temperature for 12 hours, 100ml of water was added to the reaction mixture was cooled, (50ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) washing the resulting organic phase dried over anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure to give 1- [4- (5-bromo – pyridin-2-ylmethyl) – piperazin-1-yl] -2-methyl – propan-1-one ( 282mg, oil), yield: 86%.

According to the analysis of related databases, 936342-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113293-70-2, 2,6-Dichloroisonicotinaldehyde, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

EXAMPLE 7G 2,6-dichloro-4-(dimethoxymethyl)pyridine To a solution of EXAMPLE 7F (2 g, 1 1.4 mmol) in methanol (10 mL) and toluene (10 mL) was added methyl orthoformate (2.4 g, 22.9 mmol) and p-toluenesulfonic acid (98 mg, 0.57 mmol) and the mixture was heated at reflux for 2 hours. After concentration, the residue was diluted with dichloromethane and was washed with saturated aqueous sodium carbonate and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound.

The synthetic route of 113293-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109613-97-0, 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. 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine, molecular formula is C6H7BrN2O, 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.

To a solution of 2-bromo-4-methoxy-pyridin-3-ylamine (540 mg, 2.66 mmol) in pyridine (20 mL) at 0 C is added ethyl chloroformate (0.38 mL, 3.99 mmol). After 30 min, more chloro formate is added (~18 mmol) is added until the reaction goes to completion. The mixture is partitioned between sat. NaHC03 and EtOAc. The two layers are separated, and the aqueous layer is extracted with EtOAc once. The combined organic layers are washed with H20 and brine, dried over MgS04, filterd, and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/MeOH (100/0 to 90/10) as eluant to yield 0.54 g of the product as a white crystalline solid. 1H NMR (CDC13, 300 MHz) 8.18 (d, J= 5.6, 1H), 6.84 (d, J= 5.7, 1H), 6.02 (br s, 1H), 4.23 (q, J = 7.0, 2H), 3.92 (s, 3H), 1.31 (t, J= 7.2, 3H). LC Rt: 1.89 min; LCMS m/z 275 (M+l, 100%).

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 109613-97-0, 2-Bromo-4-methoxypyridin-3-amine.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/78984; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem