Reference of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.
To a solution of 1 -methyl- lH-imidazole-4-carbaldehyde (lg, 9.1 mmol, 1.1 eq.) in THF (12 mL) is added P(Bu)3 (2.16 mL, 8.7 mmol, 1.05 eq.) and the reaction mixture is heated at 50C for 5 min. teri-butyl ester acrylate (1.2 mL, 8.3 mmol, 1 eq.) is added and the reaction mixture is stirred at 80C for 3h. teri-butyl ester acrylate (0.3 mL, 0.25 eq.) is added and this process (heating 3h and addition of tert- butyl ester acrylate) is repeated until no evolution is observed by TLC (EtOAc) and UPLC/MS. The reaction mixture is concentrated in vacuo and the residue is purified by flash chromatography on silica gel (eluting with Heptane/EtOAc 100/0 to 0/100) to afford the expected product. LCMS: MW (calcd): 238; m/z MW (obsd): 239 (M+H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.
Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; BREBION, Franck, Laurent; ALVEY, Luke, Jonathan; AMANTINI, David; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene, Marie; PEIXOTO, Christophe; VARIN, Marie, Laurence, Claire; DE CEUNINCK, Frederic, Andre; POP-BOTEZ, Iuliana, Ecaterina; (317 pag.)WO2016/102347; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem