Reference of 23579-79-5,Some common heterocyclic compound, 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a stirred solution of 4-chloro-1-tetrahydropyran-2-yl-indazol-5-amine (14.47 g, 57.50 mmol) and 3,5-dibromo-1-methyl-1H-1,2,4-triazole (13.85 g, 57.50 mmol) in dry THF (150 mL) at -20 C under N2 was added sodium bis(trimethylsilyl)amide solution (1.0 M in THF) (57.50 mL, 57.50 mmol) and the mixture stirred at 0 C for 20 min. Further sodium bis(trimethylsilyl)amide solution (1.0M in THF, 28.75 mL) was added and the reaction was stirred for 20 min. The mixture was quenched with sat. aq. NH4Cl (150 mL) and extracted with EtOAc (250 mL). The layers were separated, and the aqueous layer extracted with further EtOAc (2 x 100 mL). The combined organics were dried over MgSO4. and concentrated in vacuo. The solid residue was triturated with diethyl ether and filtered, washed with further diethyl ether to give N-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-4-chloro-1-tetrahydropyran-2-yl-indazol-5-amine (19.75 g, 47.97 mmol, 83% yield) as a white solid. UPLC-MS (ES+, Method A): 2.79 min, m/z 413.0 [M+H]+.1H NMR (400 MHz, DMSO-d6) delta 8.86 (s, 1H), 8.15 (d, J = 0.8 Hz, 1H), 7.74 (dd, J = 8.9, 0.9 Hz, 1H), 7.51 (d, J = 8.9 Hz, 1H), 5.88 (dd, J = 9.5, 2.4 Hz, 1H), 3.94-3.86 (m, 1H), 3.79-3.73 (m, 1H), 3.71 (s, 3H), 2.46-2.33 (m, 1H), 2.11-1.95 (m, 2H), 1.83-1.54 (m, 3H).
The synthetic route of 23579-79-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
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