Electric Literature of 27808-16-8, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, 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.
3-bromo-6-methylpyridine-2-carboxylic acid (408 mg, 1 .89 mmol) was dissolved in a mixture of 1 ,4-Dioxane (2ml_)Water (0.200ml_), then 4-Methyl-1 H-1 ,2,3-triazole (236 mg, 2.84 mmol), cesium carbonate (1 .24 g, 3.78 mmol), Cul (18 mg, 0.09 mmol) and (1 R,2R)-N 1 , N2-dimethylcyclohexane-1 ,2-diamine (54 mg, 0.38 mmol) were added. The mixture was stirred at 120 C for 2 hrs. Reaction mixture was cooled to RT and then water and MTBE were added. After vigorously stirring, the layers were separated and the aqueous one was acidified to pH 2 with HCI 6N. The acidic solution was concentrated and purified by RP on C18 column [eluting H20 (0.1 % HCOOH)/CH3CN from 100:0 to 60:40] affording 6-methyl-3-(4-methyl-2H-1 ,2,3-triazol-2-yl)pyridine-2-carboxylic acid (p95, 274 mg, y= 66% yield) and 6-methyl-3-(4-methyl-1 H-1 ,2,3-triazol-1 -yl)pyridine-2- carboxylic acid (p96, 40 mg, y=10%) as a white solids. P95 MS (/77/z): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.17 (d, 1 H), 7.72 (s, 1 H), 7.54 (br. s., 1 H), 2.62 (br. s., 3 H), 2.38 (s, 3 H) P96 MS (mlz): 219.2 [MH]+ 1 H NMR (MeOD-d4) delta 8.05 (s, 1 H), 7.94 (d, 1 H), 7.62 (d, 1 H), 2.67 (s, 3 H), 2.40 (s, 3 H)
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Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics