Synthetic Route of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, 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 mixture of 6-1 (50 mg, 0.13 mmol, 1.0 eq) and 6-la (28 mg, 0.17 mmol, 1.30 eq) in dioxane (2 mL) and H20 (0.5 mL) was added Na2C03 (38 mg, 0.36 mmol, 2.7 eq) and Pd(dppf)Cl2 (10 mg, 13 umol, 0.1 eq) in one portion under N2. The mixture was stirred at 100 C for 16 h. LCMS showed the starting material was consumed completely and one peak with desired MS was detected. The reaction mixture was concentrated under reduced pressure to remove solvent, and then added CH3CN (5 mL), filtered to give a black-brown liquid. The residue was purified by prep-HPLC. LCMS and XH NMR confirmed Compound 6 was obtained (2.06 mg, 5.5 umol, 4.2% yield, HC1). LCMS (ESI): RT = 0.752 min, mass calcd. For Ci6H22N402S, 334.15 m/z found 334.9[M+H]+.1H NMR (400MHz, DMSO-c) 58.76 (s, 1H), 8.34 (br s, 1H), 7.95 (d, J=2.00 Hz, 1H), 7.60 (dd, J=8.80, 2.00 Hz, 1H), 6.91 (d, J=8.80 Hz, 1H), 4.13 (s, 3H), 3.11 (s, 3H), 2.60 – 2.53 (m, 1H), 2.02 – 1.89 (m, 2H), 1.74 – 1.63 (m, 2H), 1.62 – 1.51 (m, 1H), 1.49 – 1.26 (m, 5H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methyl-1H-1,2,3-triazole, its application will become more common.
Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics