p-Fluoronitrobenzene → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

Participants

Reaction Steps

To a solution of compound 6.0 4-methyl imidazole (1 mL, 10 mmol, 1 equiv.) in DMF at room temperature was added 1-fluoro-4-nitrobenzene 6.1 (820 mg, 10 mmol, 1 equiv.) and K2CO3 (1.38 g, 10 mmol, 1 equiv.). The resulting mixture was heated to 110° c for 4h before being cooled to room temperature, filtered through celite, and washed with EtOAc (20 mL×4). The collected filtrate was further washed with brine (50 mL×3) and dried over Na2SO4. After removal of solvent, the residue was diluted with MeOH (20 mL). Pd/C (50 mg, 5% mass equiv.) was added and the reaction flask was charged with a H2 balloon and stirred overnight at room temperature. The mixture was filtered through celite and washed with EtOAc (20 mL×3). The collected filtrate was concentrated and the residue was purified via flash chromatography (hexanes:EtOAc=1:1) to afford the desired product 6.3 4-(4-methyl-1H-imidazol-1-yl)benzenamine (1.0 g; 60%). LC-MS (M+H):174.15

Provenance & Evidence