Electric Literature of 7170-01-6, 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-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.
3-Methyl-iH-i,2,4-triazole (375 mg, 4.51 mmol) was placed in a flask with dry DMF (5 mL).Sodium hydride (195 mg, 4.89 mmol) was added and the RM was stirred at room temperature for 15 minutes. tert-Butyl 4-((methylsulfonyl)oxy) pi peridi ne-i -carboxylate (Intermediate C, step 1) (i.OOg, 3.S8mmol) was then added and the RM was stirred at 10000 for 4 hours. The resulting mixture was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over Mg504, filtered and the solvent wasremoved in vacuo. The product was purified by chromatography on silica eluting with isohexane/( EtOAc:MeOH – 10:1) to afford:Product Step 1 a: tert- Butyl 4-(3-methyl- 1 H- 1,2 ,4-triazol- 1 -yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 8.40 (iH, 5), 4.48 (iH, m), 4.01 (2H, m), 2.90 (2H, m), 2.22(3H, 5), 1.99 (2H, m), 1.72 (2H, m), 1.40 (9H, 5).Product Step 1 b: tert- Butyl 4-(5-methyl- 1 H- 1,2 ,4-triazol- 1 -yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 7.79 (iH, 5), 4.45 (iH, m), 4.02 (2H, m), 2.90 (2H, m), 2.41 (3H, 5), 1.82 (2H, m), 1.75 (2H, m), 1.41 (9H, 5).
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Reference:
Patent; NOVARTIS AG; BEATTIE, David; BAETTIG, Urs; LEGRAND, Darren Mark; LISTER, Andrew Stuart; MCKENNA, Jeffrey; PEARCE, David William; SANDHAM, David Andrew; STEWARD, Oliver Ross; THOMSON, Christopher; WO2015/8230; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics