22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 22034-13-5
A 100 mL round bottom flask is charged with 4-bromobenzo[cl[1,2,Slthiadiazole (1.61 g, 7.49 mmol, 1.00 equiv), tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (2.74 g, 8.24 mmol, 1.10 equiv), potassium carbonate (3.10 g, 22.5 mmol, 3.00 equiv), and [1,1? -Bis(diphenylphosphino)ferrocenel dichloropalladium(ll) (0.274 g, 0.374 mmol, 5.00 molpercent). The flask is connected to a reflux condenser and is placed under a nitrogen atmosphere. 38 mL of nitrogen-sparged 9:1 dioxane:water is added and the mixture was stirred at 100°C overnight.The solution is cooled and quenched with water. Product is extracted with several portions of dichloromethane. Combined organic fractions are dried with Mg504, concentrated, and purified by chromatography on silica gel (20percent EtOAc in hexane). A white solid is isolated. The material is immediately dissolved in 30 mL dichloromethane and 3 mL concentrated HC1 are added. The mixture is stirred at ambient temperature overnight. The slurry is filtered, and the isolated white solid is rinsed with a few additional portions of dichloromethane. The solid is dried in a vacuum oven for several hours. Proton/CarbonNMR are consistent with the HC1-salt of the desired product. ?H NMR (500 MHz, DMSOd 6) oe 8.62 (s, 3H), 8.11 (dd, J= 8.7, 1.1 Hz, 1H), 8.06?7.96 (m, 2H), 7.88 (dd, J=7.0, 1.1 Hz, 1H), 7.82 (dd, J= 8.6, 7.0 Hz, 1H), 7.68 (d, J= 8.1 Hz, 2H), 4.11 (s, 2H). ?3C NMR (126 MHz, DMSO-d6) oe 154.95, 152.61, 136.77, 134.14, 132.71, 130.08, 129.16, 129.07, 128.01, 120.61, 41.81.
The synthetic route of 22034-13-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; YOUNG, Kaylie L.; CUMMINS, Clark H.; GLOVER, William C.; GRIGG, Robert David; (26 pag.)WO2019/27608; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary