Category: 13626-17-0

Synthetic Route of 13626-17-0, Adding some certain compound to certain chemical reactions, such as: 13626-17-0, name is 3,5-Dibromo-4-chloropyridine,molecular formula is C5H2Br2ClN, 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 13626-17-0.

Compound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99%) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28% methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88%) as a yellow solid

According to the analysis of related databases, 13626-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13626-17-0, Adding some certain compound to certain chemical reactions, such as: 13626-17-0, name is 3,5-Dibromo-4-chloropyridine,molecular formula is C5H2Br2ClN, 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 13626-17-0.

Compound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99%) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28% methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88%) as a yellow solid

According to the analysis of related databases, 13626-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13626-17-0, 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. 13626-17-0, name is 3,5-Dibromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3,5-dibromo-4-chloropyridine (X, 0.5 g, 1.84 mmol) and cyclopropylboronic acid (0.17 g, 2.02 mmol), cesium carbonate (1.19 g, 3.68 mmol ) in the mixture of 1,4-dioxan (10 mL) and water (2 mL).The reaction mass was purged with nitrogen for 15 min. Then catalyst Pd (dppf)2Cl2 (0.075 g, 0.09 mmol) was added and allowed to stir at 100 C for 4 h. The reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts were concentrated under vacuum to afford the crude compound, which was purified by column chromatography using 10-40% ethyl acetate/hexane as an eluent to obtain title compound. MS (M+l): 233.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13626-17-0, 3,5-Dibromo-4-chloropyridine, and friends who are interested can also refer to it.

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

Electric Literature of 13626-17-0, 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. 13626-17-0, name is 3,5-Dibromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3,5-dibromo-4-chloropyridine (X, 0.5 g, 1.84 mmol) and cyclopropylboronic acid (0.17 g, 2.02 mmol), cesium carbonate (1.19 g, 3.68 mmol ) in the mixture of 1,4-dioxan (10 mL) and water (2 mL).The reaction mass was purged with nitrogen for 15 min. Then catalyst Pd (dppf)2Cl2 (0.075 g, 0.09 mmol) was added and allowed to stir at 100 C for 4 h. The reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts were concentrated under vacuum to afford the crude compound, which was purified by column chromatography using 10-40% ethyl acetate/hexane as an eluent to obtain title compound. MS (M+l): 233.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13626-17-0, 3,5-Dibromo-4-chloropyridine, and friends who are interested can also refer to it.

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 13626-17-0, 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 13626-17-0 as follows.

Intermediate 24: 2-(benzeuesulfonyl)-2-(5-bromo-4-chloropyridin-3-yl)acetonitrile To a stirred and nitrogen degassed solution of 2-{benzenesulfonyflacetonitrile (CM 7605-25-9; 7.64 g, 42.20 mmol) in anhydrous DME (100 mL) was added sodium hydride (3.83 g, 96 mmol, 6o% dispersion in oil) at o C. The mixture was stirred at oC for 5 mm and then at it for 15 mm. This mixture was added to a previously nitrogen degassed solution of 3,5-dibromo-4-chloropyfldane (CM 13626-17-0; 10.40 g, 38.30 mmol), tetrakis(triphenylphosphane) palladium (i.ii g, 958 jimol) in anhydrous DME (100 mL). The reaction mixture was heated at reflux for 16 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (Ci8-silica, o-8o% acetonitrile / water (with o.i% ammonia)) to affordthe title compound. -?H NMR (400 MHz, DMSO-d6) 6 ppm 7.37 7.58 (m, 3 H) 7.67 – 7.83 (m, 3 H) 8.13 – 8.29 (m, 1 H) 8.31 – 8.44 (m, 1 H)MS ES: 372

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13626-17-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem