Category: 407-20-5

Reference of 407-20-5 ,Some common heterocyclic compound, 407-20-5, molecular formula is C5H3BrFN, 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 stirred solution of diisopropylamine (0.48 mL, 0.0034 mol) in dry tetrahydrofuran (10 mL) was added 1.6 M rc-butyl lithium in hexane (2.39 mL, 0.00369 mol) drop wise under nitrogen atmosphere at -78 C and stirred for 30 min at -78 C. To the above stirred mixture was added a solution of 3-bromo-5-fiuoropyridine (0.5 g, 0.00284 mol) in dry tetrahydrofuran at -78 C and stirred for 45 min. After 45 min, a solution of hexachloroethane in dry tetrahydrofuran was added to the above reaction mixture at -78 C and stirred for 30 min at -78 C. The reaction mixture was slowly warmed to RT and stirred for 1 h. The reaction was quenched with saturated solution of ammonium chloride (10 mL) and extracted with diethyl ether (25 mL x 3). The combined organic layer was washed with water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The obtained crude was purified with silica gel chromatography by hexane to afford the title compound. lH NMR (400 MHz,CDC13) delta: 8.58 (s, 1 H), 8.43 (s, 1 H). MS (M+l): 209.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 407-20-5, 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 407-20-5 as follows.

Preparation 10: (l-(3-amino-5-fluoropyridin-4-yl)piperidin-4-yl)(4-methylpiperazin-l- yl)methanone (hydrochloride) 17b Scheme 5 Step 1: 3-bromo-4-chloro-5-fluoropyridine hydrochloride 18 [00261] To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 min and a solution of 1, 1, 1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approximately 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 rnL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (MgS04), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown oil that turned to a crystalline solid on standing, 1 1.85 g, 89%). lH NMR (DMSO-d6) delta 8.78 (s, 1H), 8.76 (s, 1H). [00262] To a solution of 3-bromo-4-chloro-5-fluoro-pyridine (7.56 g, 32.18 mmol) in pentane (100 mL) was added hydrogen chloride (2M in ether) (17.7 mL of 2 M, 35.4 mmol). An off-white precipitate formed instantly. The mixture was stirred for 5 minutes then the solid was collected by filtration, washed with pentane and dried by suction to afford the desired product as an off-white solid (4.79 g, 60%). XH NMR (DMSO-d6) delta 8.77 (s, 1H), 8.75 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 407-20-5, 3-Bromo-5-fluoropyridine, 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, 407-20-5, blongs to pyridine-derivatives compound. Recommanded Product: 407-20-5

To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 mm and a solution of 1,1,1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approx 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 mL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (Mg504), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown oil that turned to a crystalline solid on standing, 11.85 g, 89%). ?H NMR (DMSO-d6) oe 8.78 (s, 1H), 8.76 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BOYALL, Dean; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; ETXEBARRIA I JARDI, Gorka; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PINDER, Joanne; WO2015/84384; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem