Extracurricular laboratory: Synthetic route of 4-Methyl-1H-1,2,3-triazole

According to the analysis of related databases, 27808-16-8, the application of this compound in the production field has become more and more popular.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Methyl-1H-1,2,3-triazole

To a solution of E15 (150 mg, 0.35 mmol) in DMF (6 mL) was added Cs2C03 (343 mg, 1.05 mmol) and 4-methyl-l, 2, 3-triazole (145 mg, 1.75 mmol) at 28 C. The reaction mixture was stirred at the same temperature for 6 h. TLC showed that the starting material was consumed completely. The mixture was poured into water (20 mL), and extracted with EtOAc (10 mL *2). The combined organic layers were dried over Na2SC>4 and concentrated to give crude product. The crude product was purified by pre-HPLC to give pure 94 (35.8 mg) and a mixture of 95 and 96 (20 mg). Then the mixtue was purified by SFC to give 95 (3.9 mg) and 96 (5.6 mg). Total yield: 23.7%. The structure of the three targets was confirmed by NOE. 1H NMR (94): (400 MHz, CDC13) delta 7.42 (s, 1H), 5.19-5.08 (m, 2H), 4.13-4.09 (m, 1H), 3.53- 3.38 (m, 2H), 3.29 (s, 3H), 2.61-2.54 (m, 1H), 2.33 (s, 3H), 2.26-2.15 (m, 1H), 2.11-1.95 (m, 2H), 1.78-1.61 (m, 9H), 1.52-1.06 (m, 9H) , 1.04-0.81 (m, 2H) , 0.72 (s, 3H) . 1H NMR (95): (400 MHz, CDC13) delta 7.50 (s, 1H), 5.23-5.05 (m, 2H), 4.15-4.06 (m, 1H), 3.58- 3.42 (m, 2H), 3.31 (s, 3H), 2.71-2.61 (m, 1H), 2.33-2.14 (m, 6H), 2.12-1.96 (m, 4H), 1.34-1.18 (m, 10H), 1.06-0.83 (m, 6H), 0.70 (s, 3H) . 1H NMR (96): (400 MHz, CDC13) delta 7.35 (s, 1H), 5.22-5.02 (m, 2H), 4.15-4.10 (m, 1H), 3.56- 3.39 (m, 2H), 3.31 (s, 3H), 2.67-2.61 (m, 1H), 2.39 (s, 3H), 2.29-1.88 (m, 10H), 1.33-1.22 (m, 10H), 1.02-0.97 (m, 1H), 0.92-0.84 (m, 2H) , 0.70 (s, 3H).

According to the analysis of related databases, 27808-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, Gerald; HERR, Robert, Jason; KARGBO, Robert, Borbo; WO2015/27227; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics