With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5788-58-9,4,5-Dibromopyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.,5788-58-9
Following a published method,27 28 (10.123g, 39.87mmol, 1.00 equiv), pyrimidine-5-boronic acid (37) (24.90g, 200.97mmol, 5.40 equiv), TEMPO (18.50g, 118.40mmol, 2.97 equiv), Cu(OAc)2¡¤H2O (4.20g, 21.04mmol, 0.53 equiv) and powdered 4A molecular sieves (6.7g) were combined in CH2Cl2 (300mL). To this mixture was added pyridine (3.40mL, 42.21mmol, 1.06 equiv), and the resulting khaki suspension was stirred vigorously at 20C under N2 for 15min, and then under atmospheric air (via three needles in one of the septa capping the reaction vessel). A further quantity of pyridine (15.00mL, 186.22mmol, 4.67 equiv) was then added, causing an immediate change in the colour of the reaction mixture to a blue suspension, which became a green suspension after stirring overnight. The rate of stirring was decreased and the mixture was stirred at 20C for 8.5days. The reaction was then filtered through a pad of Celite, and the filtrate was diluted, washed with saturated aqueous NaOAc, and extracted with CH2Cl2 (¡Á4). The combined organic extracts were washed (saturated aqueous NaHCO3, dried, and concentrated to dryness under reduced pressure. The resulting viscous red semi-solid was triturated with 20% EtOAc/hexanes to give 40 (9.993g) as a ?1:1 mixture with an unidentified impurity (probably starting material judged by 1H NMR), and was used without further purification: 1H NMR (CDCl3): 10.77 (v br s, 1H), 9.23 (s, 1H), 9.16 (s, 2H), 8.03 (s, 1H), 7.84 (s, 1H); HRESIMS calcd for C8H581Br2N4O m/z [M+H]+ 334.8784, found 334.8801, calcd for C8H581Br79BrN4O m/z [M+H]+ 332.8804, found 332.8820, calcd for C8H579Br2N4O m/z [M+H]+ 330.8825, found 330.8832; TLC Rf=0.18, 0.20 (20% EtOAc/hexanes).
The synthetic route of 5788-58-9 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Brooke, Darby G.; Van Dam, Ellen M.; Watts, Colin K.W.; Khoury, Amanda; Dziadek, Marie A.; Brooks, Hilary; Graham, Lisa-Jane K.; Flanagan, Jack U.; Denny, William A.; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1029 – 1039;,
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