Category: 153034-78-7

Electric Literature of 153034-78-7, 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. 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. A new synthetic method of this compound is introduced below.

(2) Synthesis of 2-fluoro-4-iodo-3,5-dimethylpyridine Diisopropylamine (88 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. in a nitrogen atmosphere. A 2.69 M solution of n-butyllithium in hexane (215 mL) was added dropwise to the solution. After completion of the dropwise addition, the mixture was warmed to -5 C. with stirring over 30 minutes. The reaction mixture was cooled to -72 C. A solution of 2-fluoro-3-iodo-5-methylpyridine (109.69 g) in TIE (240 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -74 C. for 1.5 hours. A solution of methyl iodide (36 mL) in THF (160 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at -70 C. to -74 C. for two hours. After completion of the reaction, water (200 mL) was added to the reaction mixture at the same temperature. The mixture was stirred at the same temperature for two minutes. The reaction mixture was returned to room temperature, and water (1.2 L) was then added. The mixed solution was stirred for three minutes. Water (300 mL) was further added. The mixture was extracted with MTBE (1.2 L). The organic layer was washed with brine (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. n-heptane (100 mL) was added to the residue, followed by cooling. The precipitated solid was collected by filtration. The residue was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. This operation was repeated twice to give the title compound (86.9 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.39-2.40 (m, 6H), 7.80-7.82 (m, 1H). ESI-MS m/z 252 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-78-7, 2-Fluoro-3-iodo-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 153034-78-7 ,Some common heterocyclic compound, 153034-78-7, molecular formula is C6H5FIN, 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 solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 6.3 g (87%) of the desired product. MS (DCI/NH3) m/z 238 (M+H)+; 1H NMR (CDCl3) delta 7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-78-7, its application will become more common.

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

Application of 153034-78-7, 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 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

In a 20-ml flask, 2-fluoro-3-iodo-5-methylpyridine (1.0 g, 4.2 mmol), potassium acetate (828 mg, 8.4 mmol), acetic acid (1 ml) and aniline (393 mg, 4.2 mmol) were mixed, and the solution was heated to reflux for 10 hours. After allowing the solution to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 10 hours. After allowing the mixture again to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 8 hours. This reaction solution was cooled to room temperature, ethyl acetate (20 ml) was added thereto. The organic layer was separated and washed with water (5 ml) two times. The organic layer was washed twice with a saturated aqueous sodium bicarbonate solution (10 ml) and further washed with saturated brine (10 ml) . The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, diisopropyl ether (about 50 ml) was added to the residue, and a precipitate was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane : ethyl acetate = 4:1). The obtained extract was concentrated under reduced pressure, and dried under reduced pressure at 50C, to yield the title compound (539 mg, 1.7 mmol) as a yellow oily material (yield 41.2%) . 1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.17 (s, 3H), 6.77 (brs, IH), 6.98-7.03 (m, IH), 7.28-7.34 (m, 2H), 7.53-7.57 (m, 2H), 7.77-7.79 (s, 2H), 7.96-7.97 (m, IH).13C-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 17 . 04 , 81 . 16, 119.57 , 122 .48 , 125.72 , 128. 99, 140. 60, 147 .20, 147 .93, 151 . 92 High resolution mass spectrometry (Ci2HiIlN2 )Theoretical value : 308 .9889 [M-H] + Measured value : 309. 9892 [M-H] +

According to the analysis of related databases, 153034-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-78-7 ,Some common heterocyclic compound, 153034-78-7, molecular formula is C6H5FIN, 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.

4-Chloro-3,5- dinitro-benzonitrile (200 mg, 0.88 mmol), 2-fluoro-3-iodo-5-picolione (208 mg, 0.88 mmol), and copper (45 mum powder, 168 mg, 2.6 mmol) were combined in DMF (2 mL) in a sealed tube purged with nitrogen. The reaction was heated at 150 C for 30 min in the microwave. The reaction was diluted with acetone and the solids were removed by filtration. The solution was concentrated in vacuo. The crude product was purified by silica gel chromatography (80% CH^CVhexanes) to provide the title compound as a faintly yellow solid (119 mg, 45%), which was slow to crystallize. 1H NMR (400 MHz, CDCl3): delta 8.50 (s, 2H), 8.16 (d, IH, J = 1.2 Hz), 7.42 (dd, IH, J = 8.8, 2.0 Hz), 2.38 (s, 3H). MS (ES) [m+H] calc’d for Ci3H7FN4O4, 303; found 303.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-78-7, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/129401; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem