Synthesis
General procedure: 1-fluoro-4-nitrobenzene (10 g, 70.9 mmol), 2-methyl-1H-imidazole (5.8 g, 70.9 mmol) and cesium carbonate (Cs2CO3, 34.7 g, 106.4 mmol) were placed in degassed N,N-dimethylformamide (DMF, 200 mL). The mixture was heated to 100 °C and stirred overnight under nitrogen protection. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of 1-fluoro-4-nitrobenzene, the reaction mixture was concentrated under reduced pressure. Water (300 mL) was added to the concentrated residue and a gray precipitate was precipitated, which was separated by filtration to afford the target compound 2-methyl-1-(4-nitrophenyl)-1H-imidazole (12.8 g, 89% yield).
References
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 597 - 609
[2] Patent: WO2011/75478, 2011, A1. Location in patent: Page/Page column 53
[3] Patent: WO2009/71888, 2009, A1. Location in patent: Page/Page column 83
[4] Patent: US5298520, 1994, A
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1799 - 1810
