[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.CC(C)([O-])C.[Li+].CCCCCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1F.[NH4+].[Cl-]>C1COCC1.O1CCOCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][C:25]=1[N:3]1[C:2]([CH3:1])=[CH:6][N:5]=[CH:4]1A solution of 4-methyl-1H-imidazole (1.352 g, 16.46 mmol) in 20 mL THF was treated with lithium tert-butoxide 1N in hexane (16.46 ml, 16.46 mmol) and was allowed to stir for one hour. The reaction mixture was concentrated and then transferred to a microwave vial charged with 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (2.360 ml, 16.46 mmol) and 10 mL dioxane. The reaction mixture was heated to 180° C. in a microwave reactor for one hour. After cooling to room temperature, the reaction mixture was poured into saturated NH4Cl solution and was extracted with DCM. The organics were concentrated. then purified directly by silica gel column chromatography (0 to 50% EtOAc/heptane) yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-5-methyl-1H-imidazole (0.710 g, 2.327 mmol).
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