Category: 790692-90-9

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. 790692-90-9, name is 6-Chloro-5-iodo-3-nitropyridin-2-amine, the common compound, a new synthetic route is introduced below. Product Details of 790692-90-9

A solution of palladium acetate (187 mg, 0.83 mmol) and triphenyl arsine (509 mg, 1.66 mmol) in chloroform (30 mL) was stirred for 30 min at room temperature. This solution was added to the mixture of glycal (3.25 g, 9.2 mmol), 2 (2.49 g, 8.3 mmol) and silver carbonate (4.59 g, 16.6 mmol) in chloroform (60 mL) at room temperature. The reaction mixture was refluxed overnight, cooled to room temperature and filtered through a celite pad, the filtrate was concentrated and the residue was purified by silica gel column chromatography (Hex/EtOAc=4/1 to 7/3) to give compound 3 (2.75 g, 5.23 mmol, 63%) as an orange foam. 1H NMR (CDCl3, 300 MHz) delta8.42 (s, 1H), 7.73-7.82 (m, 4H), 7.41-7.48 (m, 6H), 5.83 (nm, 1H), 7.77 (m, 1H), 4.23 (s, 1H), 3.90 (m, 2H), 1.78 (t, 1H, J=6.0), 1.23 (t, 1H, J=6.9), 1.08 (s, 9H).

The synthetic route of 790692-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Benner, Steven A; Hoshika, Shuichi; (37 pag.)US10059737; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 790692-90-9, 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. 790692-90-9, name is 6-Chloro-5-iodo-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

The compound 268-100 was prepared as follows. To a solution of 6-chloro-3-nitropyridin-2-amine (630 mg, 3.63 mmol) in ethanol (11 mL) was add I2 (920 mg, 3.62 mmol) and Ag2SO4 (1132 mg, 3.63 mmol).). The resulting solution was stirred overnight at room temperature and dissolved in water (100 mL), then extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated under vacuum to produce 6-chloro-5-iodo-3-nitropyridin-2-amine as a yellow solid (640 mg, 59%). Next, to a solution of 6-chloro-5-iodo-3-nitropyridin-2-amine (640 mg, 2.14 mmol) in ethanol (40 ml) and water (10 ml) was added Fe powder (1.93 g, 34.46 mmol) and NH4Cl (887 mg, 16.58 mmol). The resulting solution was heated to reflux for 4 h and then concentrated. The residue was dissolved in water (100 mL) and extracted with ethyl acetate (3×80 ml). The combined organic layers was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 33% ethyl acetate in petroleum ether to produce 6-chloro-5-iodopyridine-2,3-diamine as a brown solid (560 mg, 97%). The mixture of 6-chloro-5-iodopyridine-2,3-diamine (100 mg, 0.37 mmol), (2,3-dichlorophenyl)boronic acid (147.3 mg, 0.77 mmol), Pd(Ph3P)4 (42.9 mg, 0.04 mmol) and sodium carbonate (118.2 mg, 1.12 mmol) in water (5 mL) and dioxane (15 mL) was heated to reflux overnight. Then the resulting solution was quenched with water (100 mL) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine as a brown solid (80 mg, 75%). Finally, the solution of 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine (80 mg, 0.28 mmol) in trifluoroacetic acid (10 mL) and hydrochloric acid (conc., 2 mL) was heated to reflux overnight. Then the resulting mixture was quenched with water (100 mL), adjusted pH to 8 with sodium carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,3-dichlorophenyl)-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine. Trifluoroacetic acid as a off-white solid (2 mg, 2%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,790692-90-9, its application will become more common.

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem