Pyridine-derivatives

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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrNO

Intermediate 22(E)-3-Bromo-5-(3-methoxystyryl)pyridine. To a solution of diethyl 3- methoxybenzylphosphonate (5 g, 19.36 mmol) in dimethylformamide (50 mL) at room temperature was added sodium methoxide (2.092 g, 38.7 mmol) and 18-Crown- 6 (2.047 g, 7.74 mmol). After stirring at room temperature for 5 min, the reaction was cooled to 0C and treated with 5-bromonicotinaldehyde (4.32 g, 23.23 mmol) as a solid in one portion. The ice bath was removed and the reaction stirred at room temperature for 2 h. The reaction was poured into water (500 mL) with vigorous stirring. The resulting suspension was extracted with diethyl ether, washed with water (3X), then brine, dried over magnesium sulfate, and concentrated to an oil which crystallized upon standing. The solid was triturated with a minimum of ethanol (ca. 12 mL) and placed in the freezer for 72 h. The resulting solid was broken up with a spatula, collected by filtration, and rinsed with a minimum of cold ethanol to give 3.79 g (68%) as a white crystalline solid. ¾-NMR (CDC13> 500MHz) delta 8.64 (d, J=1.8, IH), 8.57 (d, J=2.1, IH), 8.00 (dd, J=2.1, 1.8, IH), 7.33 (dd, J=7.9, 7.9, IH), 7.10-7.20 (m, 2H), 7.07 (m, IH), 7.01 (d, J=16.5, IH), 6.91 (dd, J=7.6, 2.1, IH), 3.88 (s, 3H). 13C-NMR (CDC13, 126 MHz) delta 160.1, 149.5, 146.7, 137.7, 135.1, 134.8, 132.4, 130.0, 123.7, 121.1, 1 19.6, 1 14.4, 112.2, 55.4. Mass spec: 290.14 (MH)+..

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEGNAN, Andrew P.; HUANG, Hong; SNYDER, Lawrence B.; YANG, Fukang; GILLMAN, Kevin W.; PARKER, Michael F.; WO2012/64603; (2012); A1;,
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.105250-16-6, name is (2-Methylpyridin-4-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Example S4: Preparation of 4- (2-Methyl-pyridin-4-yl)-2H-pyrazol-3-ylamine; a) To a stirred mixture of 4-hydroxymethyl-2-methyl-pyridine [CAS No. 105250-16-6] (3.37 g, 27.4 mmol), potassium cyanide (3.56 g, 54.7 mmol) and 18-crown-6 (0.72 g, 2.74 mmol) in acetonitrile (75 ml) was added dropwise at 15-20C a solution of tributylphosphine (7.16 g, 30.1 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for 25 h, poured into water (100 ml) and extracted with ethyl acetate (3 x 100 ml). The combined organic layers were washed with water (3 x 100 ml), brine (100 ml) dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 4-cyanomethyl- 2-methyl-pyridine (2.26 g, 62%) as a brown oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105250-16-6, (2-Methylpyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-ROCHE AG; WO2005/40171; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886364-86-9, 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. 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile. A new synthetic method of this compound is introduced below.

A mixture of (±)-trans-N-(6-bromo-8-chloroisoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (125 mg, 0.571 mmol), bis(pinacolato)diboron (222 mg, 0.856 mmol), potassium acetate (168 mg, 1.711 mmol), and Pd(dppf)Cl2 (42.2 mg, 0.0571 mmol) in 1,4-dioxane (3 mL) was heated in a microwave at 130 C. for 45 minutes to give (±)-(8-chloro-3-((trans-2-cyanocyclopropane-1-carboxamido)isoquinolin-6-yl)boronic acid. LCMS (ESI): [M+H]+=316.0. (0975) 5-Bromo-4-methylpicolinonitrile (168 mg, 0.856 mmol) and sodium carbonate (1 mol/L) in water (2.85 ml, 2.852 mmol) were then added. The reaction mixture was heated in a microwave at 90 C. for 55 minutes. The organic layer was purified with silica gel column chromatography (0.5 to 9% methanol in dichloromethane) to give (±)-(trans-N-(8-chloro-6-(6-cyano-4-methylpyridin-3-yl)isoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (187 mg, 86.5% yield). LCMS (ESI) [M+H]+=388.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-86-9, 5-Bromo-4-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13472-58-7, 3,5-Dichloro-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, Application In Synthesis of 3,5-Dichloro-2-methoxypyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 3,5-Dichloro-2-methoxypyridine

A solution of 3,5-dichloro-2-methoxypyridine (16 g, 90 mmol) in THF(100 mL) was slowly added to a solution of LDA (53.9 ml, 108 mmol) (2M in THF) at -78 C. DMF (14 mL, 180 mmol) was added to the reaction mixture and the resulting solution stirred at -78 C for about lh. The reaction mixture was then poured into a NH4C1 saturated aqueous solution. The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic portion was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give 3,5-dichloro-2-methoxyisonicotinaldehyde (17.54 g, 90 % ). LC/MS (Table 1, Method d) Rt = 1.86 min.; MS m/z: 205, 207 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13472-58-7, 3,5-Dichloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; ARGIRIADI, Maria A.; BREINLINGER, Eric; CUSACK, Kevin P.; HOBSON, Adrian, D.; POTIN, Dominique; BARTH, Martine; AMAUDRUT, Jerome; POUPARDIN, Olivia; MOUNIER, Laurent; KORT, Michael, E.; (392 pag.)WO2016/198908; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 154237-70-4, Adding some certain compound to certain chemical reactions, such as: 154237-70-4, name is 4-Bromo-3-cyanopyridine,molecular formula is C6H3BrN2, 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 154237-70-4.

Step 3, Method 15: 4-[5-(2-Fluoroethoxy)-l-benzofuran-2-yl]pyridine-3- carbonitrile[0204] To a stirred solution of [5-(2-fluoroethoxy)-l-benzofuran-2-yl]boronic acid (120 mg, 0.54 mmol) and 4-bromo-3-cyanopyridine (98 mg, 0.54 mmol) in 1,4- dioxane (3 mL) under nitrogen were added copper(I) iodide (10 mg, 0.054 mmol), caesium fluoride (163 mg, 1.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol). The reaction mixture was degassed using a stream of nitrogen for 10 minutes then heated under a nitrogen atmosphere to 60 C and stirred for 18 hours. The mixture was concentrated, ethyl acetate (10 mL) and water (10 mL) added and the layers separated. The organic layer was washed with water (2 x 10 mL), brine (2 x 10 mL), dried over magnesium sulphate, filtered and concentrated. Purification by FCC (silica, 0-30% ethyl acetate in heptane) and recrystallisation from heptane- dichloromethane (5:2) gave the title compound 46 mg (30% yield) as a yellow solid. Example 1, Method 15: 4-[5-(2-Fluoroethoxy)-l-benzofuran-2-yl]pyridine-3- carbonitrile[0205] 5H MR (500 MHz, DMSO) 9.11 (s, 1H), 8.92 (d, J= 5.4 Hz, 1H), 8.07 (d, J = 5.4 Hz, 1H), 7.93 (s, 1H), 7.64 (d, J= 9.0 Hz, 1H), 7.40 (d, J= 2.4 Hz, 1H), 7.13 (dd, J= 9.0, 2.5 Hz, 1H), 4.78 (dt, J = 47.9, 3.8 Hz, 2H), 4.30 (dt, J = 30.1, 3.7 Hz, 2H). Tr(MET-uHPLC-AB-lOl) = 3.21 min, (ES+) (M+H)+283.

According to the analysis of related databases, 154237-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); A1;,
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.1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.Formula: C6H4BrN3

6-bromo-1H-pyrazolo[4,3-b]pyridine (400 mg, 2.0 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.4 mmol), K2CO3 (828 mg, 6 mmol), and Pd(dppf)Cl2(81.7 mg, 0.1 mmol) were dissolved in the solvent of 1,4-dioxane/H2O (v/v = 3:1, 20 mL). The resultingmixture was stirred at 80 C under Ar for 2 h. Then, the reaction mixture was evaporated to dryness.The residue was purified by flash chromatography to give compound 39 as a yellow hairy solidwith the yield of 82%. 1H-NMR (300 MHz, DMSO-d6, ppm) 13.29 (s, 1H), 8.80 (s, 1H), 8.36 (s, 1H),8.24 (s, 1H), 8.07 (s, 2H), 3.90 (s, 3H). ESI-MS: C10H10N7O2S, Exact Mass: 199.09, m/z 200.0 (M + 1)+.Retention time 2.51 min, >95% purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Alan; Liu, Qiufeng; Wang, Ruifeng; Wei, Peng; Dai, Yang; Wang, Xin; Xu, Yechun; Ma, Yuchi; Ai, Jing; Shen, Jingkang; Ding, Jian; Xiong, Bing; Molecules; vol. 23; 3; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 21427-62-3, 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 21427-62-3 as follows.

To a solution of 129.2 g (0.69 mol) of 2,5-dichloro-3-nitropyridine in 1300 ml of dioxane is added 26 0 g of Raney-nickel, that has previously been washed with ethanol. This mixture is then hydrogenated with hydrogen under normal pressure at 20-35 C. After uptake of 20% of the theoretical amount of hydrogen, another 30 g of washed Raney-nickel catalyst are added. After hydrogenating for 22 hours, the catalyst is filtered off, the solvent is evaporated and the residue is crystallized from hexane/ ethyl acetate. Thus, 84.9 g of 3-amino-2,5-dichloropyridine (78% of the theory) are obtained, which melts at 129-132 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21427-62-3, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4935051; (1990); A;,
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. 15128-89-9, name is 3-Hydroxy-4-methyl-2-nitropyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a solution of 4-methyl-2-nitropyridin-3-ol (4.85 g) in methanol (90 mL) was added 28% sodium methoxide solution in methanol (6.3 mL) . The solution was stirred at room temperature for 15 min and then cooled with an ice-bath. A solution of bromine (1.6 mL) in methanol (15 mL) was added dropwise, and the reaction mixture was stirred at 00C for 2 hr and concentrated to give crude 6-bromo-4-methyl-2- nitropyridin-3-ol, which was used for the next step without further purification. To a mixture of crude 6-bromo-4- methyl-2-nitropyridin-3-ol and potassium carbonate (8.70 g) in acetone (70 mL) was added ethyl bromoacetate (3.5 mL) . The mixture was refluxed for 15 hr and the solvent was evaporated. DMSO (50 mL) , potassium carbonate (5.00 g) and ethyl bromoacetate (1.5 mL) were additionally added, and the mixture was stirred at room temperature for 60 hr, poured into water and extracted with ethyl acetate. The extract was washed with 5% aqueous Na2S2O3, water and saturated aqueous NaHCO3, dried over MgSO and concentrated. The residue was chromatographed on silica gel using n- hexane/ethyl acetate as an eluent to give the title compound as an oil (7.40 g) .1H-NMR (300 MHz, CDCl3) delta: 1.31 (t, J = 6.6 Hz, 3H), 2.47 (s, 3H), 4.27 (q, J = 6.6 Hz, 2H), 4.60 (s, 2H), 7.59 (s, IH).

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, 15128-89-9, 3-Hydroxy-4-methyl-2-nitropyridine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/77961; (2007); A2;,
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

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