Uses
7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is an important chemical reagent that can be used to prepare heteroaryl compounds. The synthetic product can effectively inhibit necrosis and thus finds application in the treatment of diseases and conditions related to the necrosis pathway, including, for example, inflammation, tumors, metabolic diseases, and neurodegenerative diseases such as cerebral ischemia and stroke.
Synthesis
7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is prepared by reacting 6-bromo-1H-pyrrolo[3,2-b]pyridine with pyridine and cyclohexyl carbonochloridate in anhydrous THF solution. The specific reaction process is as follows: To a solution of 6-bromo-1H-pyrrolo[3,2-b]pyridine (97 mg, 0.5 mmol) in anhydrous THF (5 mL) was added slowly pyridine (120 mg, 1.5 mmol) followed by cyclohexyl carbonochloridate (162 mg, 1 mmol) in THF (2 mL). The mixture was stirred at room temperature for 3 h. The reaction was quenched by the addition of saturated NaCl solution (20 mL). The aqueous phase was extracted with EtOAc (3×) and the combined organic layers were combined, dried and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to give 7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one as a colorless oily liquid (120 mg, 75%).1H NMR (400 MHz, DMSO-d6) d 8.58 (s, 2H), 7.84 (d, J = 2.4 Hz, 1H), 8.77 (d, J = 3.6 Hz, 1H), 5.13-5.00 (m, 1H), 2.13-1.97 (m, 2H), 1.91-1.75 (m, 2H), 1.72- 1.33 (m, 6H).
