A common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, its 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. 288-36-8.
To a 20 ml microwave vial containing 2-bromo-4,5-dimethoxybenzoic acid (3 g, 1 1 .5 mmol), copper iodide (0.04 g, 0.5 mol%), cesium carbonate (7.5 g, 23 mmol), triazole (1 .33 mL, 23 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.36 mL, 2.3 mmol) was added DMF (12 mL). The resulting clumpy yellow slurry was stirred until evenly dispersed then heated to 120C for 10-20 min using a microwave. At this point the reaction mixture appeared as a blue slurry which was then diluted with 20 mL ether and 20 mL H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 mL ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 mL cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure which was purified by FCC (0-5% MeOH in DCM w/ 0.5% AcOH) to afford 2,3-dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid (60%) and 2,3- dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid (20%). Data for 2,3-dimethoxy-6- [1 ,2,3]triazol-2-yl-benzoic acid, MS (ESI): mass calculated for CnHnN3O4, 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.87 (s, 2H), 7.47 (s, 1 H), 7.18 (s, 1 H), 3.94 (s, 3H), 3.91 (s, 3H).; Intermediate 80: 2,3-Dimethoxy-6-[1 , 2, 3]triazol-1 -yl-benzoic acid.The title compound was isolated from the procedure used to prepareIntermediate 79 with a 20% yield. MS (ESI): mass calculated for Cn Hn N3O , 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.17 (d, J = 1 .0 Hz, 1 H), 7.82 (d, J = 1 .0 Hz, 1 H), 7.62 (s, 1 H), 7.09 (s, 1 H), 3.95 (s, 3H), 3.91 (s, 3H).
The synthetic route of 1H-1,2,3-Triazole has been constantly updated, and we look forward to future research findings.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics