Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 101990-70-9, 5-(Chloromethyl)-2-methoxypyridine, 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 101990-70-9, blongs to pyridine-derivatives compound. Product Details of 101990-70-9

To a stirred solution of compound 2 (400 mg, 1.79 mmol) in DMF (4 mL) at 0 C, was added NaH (90 mg of a 60% dispersion in mineral oil, 2.25 mmol). The mixture was warmed to RT and stirred for 20 mm. The mixture was cooled to 0 C, and a solution of 5-(chloromethyl)-2- methoxypyridine (310 mg, 1.97 mmol) in DMF (1 mL) was added. The mixture was allowed to warm to RT and stirred for a further 16 h. The mixture was partitioned between water (50 mL)and EtOAc (30 mL). The organic layer was separated and the aq. layer re-extracted with additional EtOAc (30 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified (silica gel; eluting with 0-100% EtOAc in hexanes), to afford compound 3 (580 mg, 85%) as a colorless oil. LCMS Mass: 345.0 (M+1).

The synthetic route of 101990-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 81167-60-4, 4-(tert-Butyl)-2-chloropyridine, 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, 81167-60-4, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 2-chloro-4-terbutylpyridine (1.79 g, 10.5 mmol), 2,6-difluoro-3-pyridylboronic acid (2.6 g, 16.4 mmol), Pd(PPh3)4 (400 mg, 0.35 mmol), 2M aqueous solution of potassium carbonate (25 ml, 50 mmol) and 1,4-dioxane (80 ml) was deaerated by bubbling nitrogen through the mixture for 15 minutes. The mixture was stirred at 70C (bath) for 15 hours. The mixture was evaporated to a volume of approximately 30 ml. The residue was extracted with hexane (2 X 30 mL). The organic layers were washed with brine (20 mL) and dried over MgS04. After the evaporation of the solvent the product was purified by column chromatography (silicagel, ethyl acetate/hexane 1/2) and dried in high vacuum at room temperature. Yield 2.3 g, 88 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81167-60-4, its application will become more common.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL COMPANY LIMITED; STEUDEL, Annette; KOZHEVNIKOV, Valery; WO2014/9716; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88511-27-7, 4-Amino-3-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, Recommanded Product: 88511-27-7, blongs to pyridine-derivatives compound. Recommanded Product: 88511-27-7

Step 2. To a 2 L 3-necked flask was added DMF (700 mL), triethylene diamine ( 168 g, 1 .5 mol), and 4-amino-3-iodopyridine (24, 1 10 g, 0.5 mol). The mixture was cooled with an ice-water bath and pyruvic acid (1 32 g, 1 .5 mol) was slowly added, followed by palladium acetate (4.49 g, 0.02 mol). Under nitrogen atmosphere, the mixture was heated to 1 15 C. The reaction generated effervescence. The reaction mixture was kept at 115- 120 C for 1 1 h, The mixture was concentrated under reduced pressure The residue was poured into water (500 mL), and concentrated HC1 was added to adjust pH to The above cake was added into 500 mL of water. Concentrated HCl was added (to ensure complete protonation) followed by 5 g of active carbon. The mixture was heated to reflux for 20 min and then filtration was performed while hot. The solid was discarded and the hot filtrate was placed in a refrigerator to allow the HCl salt of the desired product to precipitate. Upon cooling, filtration was performed which afforded a dark brown solid with a wet weight of 48 g as the HCl salt of the desired product. The solid was then added to 250 mL of water and the mixture was heated until a clear solution resulted. Solid NaOH was slowly added to adjust pH to 5-6, then active carbon and an addtional 500 mL of water was added. The mixture was heated to reflux for 30 min, then filtration was performed while hot. The resulting cake was added to 750 mL of water, heated to reflux, and filtered again. The cake thus obtained was discarded. The two batches of filtrate were combined and cooled in a refrigerator. The resulting precipitate was collected by vacuum filtration, then washed with ethanol to give the title compound as a slightly yellow solid (25 g, 31 %). MS (m/z, ES-): 161 . 1 [M-1], 323. 1 [2M-1]. 1H NMR (DMSO-d6, 400 MHz) delta 12.20 (br s, 1H), 8.97 (s, 1H), 8.27 (d, J = 5.6 Hz, 1 H), 7.41 (d, = 6.0 Hz, 1H), 7.23 (s, 1H).

The synthetic route of 88511-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); 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. 5470-22-4, name is 4-Chloropicolinic acid, molecular formula is C6H4ClNO2, 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: 4-Chloropicolinic acid

A mixture of 4-chloropicolinic acid (10.0 g, 63.4 mmol), thionyl chloride (40 ml) and a catalytic amount of DMF were heated at 80 C for 3 h. Then the reaction mixture was cooled to room temperature and evaporated under reduced pressure. The residue was dissolved in 30 ml of CH2Cl2 in an ice-bath, then added to a 25% aqueous solution of ammonia (60 ml) at a rate which kept the internal temperature below 7 C with constant stirring. After 1 h, the precipitate was filtrated, washed with water (3 × 50 ml) and dried in vacuo to afford compound 2 (9.2 g, 93% yield) as a yellow solid, mp 161-162 C; 1H NMR (DMSO-d6, 400 MHz): delta 7.74-7.76 (dd, J = 1.8 and 5.3 Hz, 1H), 7.80 (br s, 1H), 8.03 (d, J = 1.8 Hz, 1H), 8.20 (br s, 1H), 8.62 (d, J = 5.3 Hz, 1H); ESI-MS m/z: 157[M+H]+; Anal. Calcd for C6H5ClN2O (%): C 46.03, H 3.22, N 17.89; Found: C 45.98, H 3.27, N 17.94.

With the rapid development of chemical substances, we look forward to future research findings about 5470-22-4.

Reference:
Article; Zhan, Wenhu; Li, Yanyang; Huang, Weiping; Zhao, Yanjin; Yao, Zhenglin; Yu, Shanyou; Yuan, Shoujun; Jiang, Falong; Yao, Shan; Li, Shuxin; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4323 – 4329;,
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.13534-97-9, name is 6-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2

To a solution of 3-amino-6-bromopyridine (1.1 g, 6.4 mmol) in THF (7 mL)-MeOH (7 mL) at RT was added phenylboronic acid (1.60 g, 12.8 mmol), PXPd (69 mg, 0.13 mmol), followed by K2CO3 (3.54 g, 25.6 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for 16 h. After cooling to RT, the reaction mixture was poured into water (10 mL), and the resultant mixture was extracted with EtOAc (3.x.40 mL). The combined organic layers were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (30-100percent) in hexane to give the title compound as an off-white solid (940 mg, 86percent). LC/MS (method A): retention time=1.28 min, (M+H)+=171.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sun, Chongqing; Ewing, William R.; Huang, Yanting; US2006/154955; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88511-27-7, 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 88511-27-7, name is 4-Amino-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-iodopyridin-4-amine (6 g, 27.2 mmol) in dioxane (135 mL), (2,6-dichloropyridin-3-yl)boronic acid (7.29 g, 38.1 mmol), and 1M Na2CO3 aqueous solution (3 eq) were added andthe reaction mixture was degassed with argon for 20 mm. ThenBis(triphenylphosphine)palladium(ll) dichloride (3.79 g, 5.4 mmol) was added and the reactionmixture was heated at 100C for 16h. After completion of reaction, the reaction mixture wasfiltered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography toafford 2,6-dichloro-[3,3-bipyridin]-4-amine (ii) (2.9 g, Yield 44%).1H NMR (400 MHz, DMSO-d6) 66.04 (s, 2H), 6.62 (d, J= 5.8 Hz, 1H), 7.71 -7.55 (m, 1H), 7.94- 7.75 (m, 2H), 8.03 (d, J = 5.7 Hz, 1 H).MS (ESI) m/e (M+1): 240.05

According to the analysis of related databases, 88511-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; VERMEIREN, Celine; (23 pag.)WO2018/24642; (2018); 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. 581-45-3, name is 4-(Piperidin-4-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 581-45-3

General procedure: The cis epoxide precursor (±)-2 was synthesized as already described [27]. In brief, elimination of water from cyclohexane-1,4-diol gave cyclohex-3-enol [40] which was epoxidized diasterioselectively by using tert-butyl hydroperoxide and Mo(CO)6 [41] to obtain the racemic epoxy alcohol. Subsequent O-p-fluorobenzylation resulted in the cis-epoxide (±)-2. To synthesize the 4-O-p-fluorobenzyl ether vesamicol derivatives (±)-3a -(±)-3m, the amine (1.41 mmol) and (±)-2 (1.12 mmol) were dissolved in 5 mL EtOH and stirred at 65-70 C for 5 days. The crude product was purified by column chromatography (silica gel 60) or by crystallization (details described for each compound). To synthesize the 5-O-p-fluorobenzyl ether vesamicol derivatives (±)-4a -(±)-4m, the cis-epoxide (±)-2 (1.12 mmol) and LiClO4 (1.97 mmol) were dissolved in 3 mL CH3CN and stirred for 10 min. Subsequently, the amine (1.41 mmol) was added and the reaction mixture was stirred at rt for 24 h. Products were purifiedby column chromatography (silica gel 60) or by crystallization (details described for each compound). The regioisomeric purity was checked by HPLC. (±)-4m (±)-5-(4-fluorobenzyloxy)-2-(4-(pyridin-4-yl)piperidin-1-yl)cyclohexanol: The crude product was purified by column chromatography using CHCl3/MeOH/NH3 (10/1/0.1). Adding of n-hexaneto a concentrated CHCl3 solution of (±)-4m and keeping afew days at 4 C resulted in the formation of 263 mg (61%) of a colorless solid.

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, 581-45-3, 4-(Piperidin-4-yl)pyridine.

Reference:
Article; Barthel, Claudia; Sorger, Dietlind; Deuther-Conrad, Winnie; Scheunemann, Matthias; Schweiger, Stephanie; Jaeckel, Petra; Roghani, Ali; Steinbach, Joerg; Schueuermann, Gerrit; Sabri, Osama; Brust, Peter; Wenzel, Barbara; European Journal of Medicinal Chemistry; vol. 100; (2015); p. 50 – 67;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 886365-02-2 , The common heterocyclic compound, 886365-02-2, name is 5-Bromo-4-methylpyridine-2-carboxylic acid, molecular formula is C7H6BrNO2, 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 solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H2SO4 (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0 C., neutralized with saturated NaHCO3, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49%) as white solid.

The synthetic route of 886365-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Bhagirath, Niala; Du Bois, Daisy Joe; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Wilhelm, Robert Stephen; US2013/158040; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5683-33-0, 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.5683-33-0, name is 2-(Dimethylamino)pyridine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.

To a solution of the (2R)-2-phenylpropylamine (1.2g, 8.87 mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and is dimethylaminopyridine (0.30 g, 2.47 mmol). Cooled reaction to 5 C., then added a solution of isopropylsulfonyl chloride (0.97 mL, 8.69 mmol) dissolved in methylene chloride (6.0 mL) over a period of 15.0 minutes. Stirred for 45.0 minutes, then stirred at room temperature for 120.0 minutes. Quenched reaction with 1N HCl (20.0 mL) and extracted organic with methylene chloride (25.0 mL). Dried organic layer with anhydrous magnesium sulfate, filtered and concentrated filtrate to provide the final title compound, ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine, (1.93 g, 90.1%) an oil; 1H nmr (CDCl3, 300 MHz) delta 1.25 (d, 3H, J=6.9 Hz), 1.29 (d, 3H, J=6.9 Hz), 1.30 (d, 3H, J=7.2 Hz), 2.98 (m, 1H), 3.05 (m, 1H), 3.22 (m, 1H), 3.36 (m, 1H), 3.89 (b, 1H), 7.23 (m, 2H), 7.34 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 5683-33-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aikins, James Abraham; Fray, Andrew Hendley; Miller, William David; Ornstein, Paul Leslie; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/233015; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13600-42-5, 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 13600-42-5 as follows.

500 mL round bottom flask, 79.6 g (330 mmo 1) of 2,6-dichloro-3-cyano-4-(trifluoromethyl)pyridine concentrated sulfuric acid 400 grams heated to 100 degrees with stirring l h, after the reaction was added to the water to precipitate a solid, filtered and washed, dried to give a white solid 77 grams, yield 90.09%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13600-42-5, its application will become more common.

Reference:
Patent; Hebei Lan Tai Chemical Technology Co., Ltd.; Guo Ming; Meng Shuiqiang; Tian Penghui; Hou Jianjun; (14 pag.)CN107382848; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem