Reference of 4278-08-4, These common heterocyclic compound, 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole, 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.
To a stirring mixture of Intermediate RR-1 (112 mg, 0.338 mmol) in 0.7 mL of DMSO, 2-(4-fluorophenyl)-lH-imidazole (109 mg, 0.67 mmol) was added. The reaction mixture was placed in a 120 C oil bath for 2 h. The crude mixture was directly loaded and purified by silica gel chromatography to give the coupled nitro ester. LCMS: 457.1 m/z (M+H)+. To a stirring mixture of the coupled nitro ester in 1.2 mL of MeOH, Pt/C (42 mg) was added and the reaction mixture was placed under 1 atm of hydrogen for 2 h. The hydrogen balloon was removed and VO(acac)2 (5 mg) was added. This reaction mixture was placed under 1 atm of hydrogen overnight. The crude mixture was filtered through a plug of Celite and the plug was washed several times with EtOAc. The filtrate was concentrated under reduced pressure. To this cyclized product, 0.5 mL of dioxane, potassium bicarbonate (100 mg) and trimethylphosphate (200 mg) were added. The reaction mixture was warmed to 100 C for several hours. The crude product mixture was cooled to rt and diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were dried over MgS04, filtered, and concentrated under reduced pressure. The resulting material was purified by preparative HPLC to give the title compound. LCMS: 409.1 m/z (M+H)+; ret. Time 4.07 min (Analytical MethodD).
The synthetic route of 4278-08-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem