Reference of 27808-16-8, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
Description D34: methyl 6-methyl-3-(4-methyl-2H-l,2,3-triazol-2-yl)-2- pyridinecarboxylate (D34); DMF (1.5 ml) was added to a mixture of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D27 (200 mg), 4-methyl-lEta-l,2,3-triazole (120 mg, 1.444 mmol), (lR,2R)-N,N’-dimethyl- 1 ,2-cyclohexanediamine (20.54 mg, 0.144 mmol), copper(I) trifluoromethanesulfonate benzene complex (18.17 mg, 0.036 mmol) and cesium carbonate (470 mg, 1.444 mmol) in a screw-topped vial. The mixture was degassed via 3 vacuum/nitrogen cycles and heated with shaking in a PLS reaction station to 120 0C for 5 hours. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water/MeOH (1 :1, 3 ml) and acidified to pH=2 by addition of 2 M HCl solution. The resulting mixture was evaporated to dryness under reduced pressure then the residue was triturated with DCM/MeOH (3:1, 5 ml). The mixture was filtered washing with more DCM/MeOH (3:1, 5 ml). The filtrate was treated with TMS-diazomethane solution 2 M in hexane (4 ml, 8 mmol) to re-esterify the acid. The reaction mixture was evaporated under reduced pressure and the residue was purified via Biotage (20%-50% EtOAc/cyclohexane; SNAP 25 silica column) to give the title compound D34 (121 mg) as colourless solid.UPLC (Acid QC POS 50-800): rt = 0.59 minutes, peak observed: 233 (M+l) C11H12N4O2 requires 232. 1H NMR (400 MHz, CDCl3y) delta ppm 8.15 (d, 1 H), 7.59 (s, 1 H), 7.37 (d, 1 H), 3.92 (s, 3 H), 2.66 (s, 3 H), 2.40 (s, 3 H).
Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 4-Methyl-1H-1,2,3-triazole.
Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics