Category: 2369-19-9

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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2369-19-9

(1) Synthesis of 2-fluoro-3-iodo-5-methylpyridine A 2.69 M n-butyllithium hexane solution (224 mL) was added dropwise to a mixture of diisopropylamine (92 mL) and THF (1.2 L) at -18C under a nitrogen atmosphere. Upon completion of the dropwise addition, the mixture was stirred while raising the temperature to -5C over a period of 20 minutes. The reaction mixture was cooled to -73C, and then a solution of 2-fluoro-5-methylpyridine (61 g) in THF (240 mL) was added dropwise thereto. The reaction mixture was stirred at -75C for 3.5 hours. A solution of iodine (139 g) in THF (24 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -75C for 1 hour and 55 minutes. Upon completion of the reaction, water (220 mL) was added to the reaction mixture at the same temperature. The mixture was stirred for 5 minutes at the same temperature. The reaction mixture was warmed to room temperature, and then water (1.2 L) was added. An aqueous sodium thiosulfate pentahydrate (136 g) solution (300 mL) and water (300 mL) were added to the mixture, and the resultant was stirred for 10 minutes. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layer was extracted with MTBE (1 L). The combined organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure. After adding n-heptane to the residue, the mixture was cooled. The precipitated solid was filtered out, and then was rinsed with n-heptane. The filtrate was cooled and the precipitated solid was filtered out. This procedure was repeated 5 times to obtain the title compound (109.69 g). 1H-NMR (400 MHz, CDCl3) delta (ppm):2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). ESI-MS m/z 238 [M+H]+

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; NORIMINE, Yoshihiko; SATO, Nobuaki; ISHIHARA, Yuki; TAKEDA, Kunitoshi; (65 pag.)EP2982674; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

Intermediate 8:2-fluoro-5-methylnicotinic acid[00363] A 1.6M solution of butyl lithium in hexanes (28.13 ml, 45 mmol) was added dropwise to a solution of diisopropylamine (6.36 ml, 45 mmol) in tetrahydrofuran (80 ml) keeping the temperature at -78C. After complete addition, the mixture was allowed to warm up to 0C, then stirred at 0C for 10 minutes. The resulting mixture was cooled down to -78C and a solution of 2-fluoro-5-methylpyridine (4.64 ml, 45 mmol) in tetrahydrofuran (15 ml) was added dropwise. The reaction mixture was stirred at -78C for 2 hours then quenched by addition of an excess of CO2 solid. The mixture was allowed to warm up to room temperature. The mixture was acidified with 10% citric acid, diluted with ethyl acetate. The organic layer was collected, washed further with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to leave the desired compound as a white solid (4.9 g, 70% yield).[00364 ] 1H NMR (DMSO-d6, 400 MHz) delta 2.34 (3H, s), 8.20-8.26 (2H, m); MS (ES+) 156, (ES”) 154.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2369-19-9 , The common heterocyclic compound, 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

EXAMPLE 38A 2-fluoro-4-iodo-5-methylpyridine A solution of dilsopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2369-19-9, 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 2369-19-9, name is 2-Fluoro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (252 mL, 1.80 mmol) in anhydrous tetrahydrofuran (5 mL) was added under argon at 20 C, a 2.5 M solution of n-butyllithium in hexanes (719 mL, 1.80 mmol). After stirring at 20 C for 30 min, the reaction was cooled to 78 C, then a solution of 2-fluoro-5-methylpyridine (14) [27] (200 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added over 10 min. The reaction was stirred at 78 C for 3.5 h, then a solution of iodine (457 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added. The mixture was stirred at 78 C for additional 1 h, before quenching with a solution of water (2 mL) and tetrahydrofuran (10 mL). After warming to 0 C, the mixture was diluted with water (50 mL) and sodium bisulfite was added until a colorless solution was obtained. After extraction with dichloromethane (3 x 30 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/cyclohexane, 5/5, v/v) to give 2-fluoro-3-iodo-5-methylpyridine (15) (275 mg, 1.16 mmol) as a colorless solid. Yield 65%; Rf (SiO2, dichloromethane/cyclohexane, 5/5, v/v) 0.21; mp 40-45 C; IR (KBr) nu 1049, 1379, 1446, 2930 cm-1; 1H NMR (200 MHz, CDCl3) delta 2.28 (s, 3H, CH3), 7.95 (m, 2H, H-4, H-6); 13C NMR (50 MHz, CDCl3) delta 17.0 (CH3), 75.4 (d, 2JC-F = 44 Hz, C-3), 132.7 (d, 4JC-F = 5 Hz, C-5), 146.8 (d, 3JC-F = 13 Hz, C-6), 150.4 (C-4), 160.4 (d, 1JC-F = 232 Hz, C-2); 19F NMR (470 Mz, CDCl3) 61.7; ESI-MS m/z 237.89 [M+H]+.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2369-19-9, 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 2369-19-9, name is 2-Fluoro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (252 mL, 1.80 mmol) in anhydrous tetrahydrofuran (5 mL) was added under argon at 20 C, a 2.5 M solution of n-butyllithium in hexanes (719 mL, 1.80 mmol). After stirring at 20 C for 30 min, the reaction was cooled to 78 C, then a solution of 2-fluoro-5-methylpyridine (14) [27] (200 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added over 10 min. The reaction was stirred at 78 C for 3.5 h, then a solution of iodine (457 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added. The mixture was stirred at 78 C for additional 1 h, before quenching with a solution of water (2 mL) and tetrahydrofuran (10 mL). After warming to 0 C, the mixture was diluted with water (50 mL) and sodium bisulfite was added until a colorless solution was obtained. After extraction with dichloromethane (3 x 30 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/cyclohexane, 5/5, v/v) to give 2-fluoro-3-iodo-5-methylpyridine (15) (275 mg, 1.16 mmol) as a colorless solid. Yield 65%; Rf (SiO2, dichloromethane/cyclohexane, 5/5, v/v) 0.21; mp 40-45 C; IR (KBr) nu 1049, 1379, 1446, 2930 cm-1; 1H NMR (200 MHz, CDCl3) delta 2.28 (s, 3H, CH3), 7.95 (m, 2H, H-4, H-6); 13C NMR (50 MHz, CDCl3) delta 17.0 (CH3), 75.4 (d, 2JC-F = 44 Hz, C-3), 132.7 (d, 4JC-F = 5 Hz, C-5), 146.8 (d, 3JC-F = 13 Hz, C-6), 150.4 (C-4), 160.4 (d, 1JC-F = 232 Hz, C-2); 19F NMR (470 Mz, CDCl3) 61.7; ESI-MS m/z 237.89 [M+H]+.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

Example 38A 2-fluoro-4-iodo-5-methylpyridine A solution of diisopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2369-19-9, 2-Fluoro-5-methylpyridine, 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, Quality Control of 2-Fluoro-5-methylpyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Fluoro-5-methylpyridine

Diisopropylamine (92 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. under a nitrogen atmosphere. To this solution was added dropwise a solution (224 mL) of 2.69 M n-butyllithium in hexane. After the dropwise addition, the temperature was increased to -5 C. over 20 minutes while stirring this mixture. The reaction solution was cooled to -73 C. To this reaction solution was added dropwise a THF solution (240 mL) of 2-fluoro-5-methylpyridine (61 g). The reaction mixture was stirred at -75 C. for three and a half hours. To this reaction solution was added dropwise a THF solution (24 mL) of iodine (139 g). The reaction mixture was stirred at -75 C. for 1 hour and 55 minutes. After the reaction, water (220 mL) was added to the reaction solution at the same temperature. The mixture was stirred at the same temperature for 5 minutes. The reaction solution was brought back to room temperature, and then water (1.2 L) was added. To this mixture were added an aqueous solution (300 mL) of sodium thiosulfate pentahydrate (136 g) and water (300 mL), and the mixture was stirred for 10 minutes. This mixture was extracted with MTBE (1.2 L). The organic layer was washed with saturated saline (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. n-Heptane was added to the residue, and the mixture was cooled. The precipitated solid was collected by filtration. The solid was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. The procedure was repeated 5 times to give the title compound (109.69 g). (0167) 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). (0168) ESI-MS m/z 238 [M+H]+

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Ozaki, Shunsuke; (31 pag.)US2016/46623; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

Example 38A 2-fluoro-4-iodo-5-methylpyridine A solution of diisopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2369-19-9, 2-Fluoro-5-methylpyridine, 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, Quality Control of 2-Fluoro-5-methylpyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Fluoro-5-methylpyridine

Diisopropylamine (92 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. under a nitrogen atmosphere. To this solution was added dropwise a solution (224 mL) of 2.69 M n-butyllithium in hexane. After the dropwise addition, the temperature was increased to -5 C. over 20 minutes while stirring this mixture. The reaction solution was cooled to -73 C. To this reaction solution was added dropwise a THF solution (240 mL) of 2-fluoro-5-methylpyridine (61 g). The reaction mixture was stirred at -75 C. for three and a half hours. To this reaction solution was added dropwise a THF solution (24 mL) of iodine (139 g). The reaction mixture was stirred at -75 C. for 1 hour and 55 minutes. After the reaction, water (220 mL) was added to the reaction solution at the same temperature. The mixture was stirred at the same temperature for 5 minutes. The reaction solution was brought back to room temperature, and then water (1.2 L) was added. To this mixture were added an aqueous solution (300 mL) of sodium thiosulfate pentahydrate (136 g) and water (300 mL), and the mixture was stirred for 10 minutes. This mixture was extracted with MTBE (1.2 L). The organic layer was washed with saturated saline (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. n-Heptane was added to the residue, and the mixture was cooled. The precipitated solid was collected by filtration. The solid was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. The procedure was repeated 5 times to give the title compound (109.69 g). (0167) 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). (0168) ESI-MS m/z 238 [M+H]+

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Ozaki, Shunsuke; (31 pag.)US2016/46623; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2369-19-9, Adding some certain compound to certain chemical reactions, such as: 2369-19-9, name is 2-Fluoro-5-methylpyridine,molecular formula is C6H6FN, 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 2369-19-9.

(a) 26.5 mL of n-butyllithium (1.57 mol/L hexane solution) was dropwise added at -78C to a solution having 4.02 g (39.8 mmol) of diisopropylamine dissolved in 70 mL of tetrahydrofuran, followed by stirring for 30 minutes. To this solution, a solution having 4.42 g (39.8 mmol) of 2-fluoro-5-methylpyridine dissolved in 18 mL of tetrahydrofuran was added, followed by stirring for 4 hours. Then, a solution having 10.1 g (39.8 mmol) of iodine dissolved in 27 mL of tetrahydrofuran was added, followed by stirring for 2 hours. 16 mL of water and 120 mL of an aqueous sodium thiosulfate solution were added, and extraction with ethyl ether was carried out. Then, the organic layer was dried over magnesium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 3.15 g (yield: 33%) of 2-fluoro-3-iodo-5-methylpyridine.1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 2.27(s, 3H), 7.95(m, 2H)

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. 2369-19-9, 2-Fluoro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1559320; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem