Synthetic Route of 6945-67-1, 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 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.
The crude title compound from Step A above was dissolved in a mixture of degassed 1 ,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 , 1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~1 15C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 00/0) to afford a mixture of the title compound and byproducts (0.076 g). Step C (0310) The mixture of the title compound from Step B above and byproducts (0.076 g) was dissolved in dichloromethane (10 mL) and trifluoroacetic acid (2.4 mL) was added. The reaction mixture was stirred at room temperature for 6 hours and then methanol was added (10 mL). The solvents were evaporated in vacuo and the residue suspended in methanol (10 mL). The solvents were again evaporated in vacuo and the residue suspended in dichloromethane (4 mL). After the addition of triethylamine (2 mL, 14.4 mmol), di-terf-butyl dicarbonate (0.2 g, 0.86 mmol), and 4-(dimethylamino)-pyridine (0.0036 g, 0.028 mmol), the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (40 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents removed in vacuo. The residue was purified on silica (25 g puriFlash, Interchim) using a Biotage I solera One purification system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the Comparative Example C9 (F-9) Precursor and the byproduct as -1 .1 -mixture (0.0231 g, pale yellow solid). 1H NMR (400 MHz, CDCI3) delta = 9.38 (d, 1 Eta), 9.35 (d, 1 H), 9,31 (s, 2H), 9.02 (d, 1 H), 8.76- 8.70 (m, 5H), 8.68 (d, 1 H), 8.55 (d, 1 H), 8.43-8.37 (m, 3H), 8.12 (dd, 1 H), 8.07 (dd, 1 H), 7.43 (d, 1 H), 7.41 (d, 1 H), 1.82 (s, 18H) (0311) MS (ESI): m/z = 291.94 [MH-Boc of the title compound]’, 170.04 [MH+-Boc of byproduct]*
According to the analysis of related databases, 6945-67-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; (72 pag.)WO2018/15546; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem