HCID 66859203, compound → HCID 58075671, compound

Participants

Reaction Steps

Step N (4): 10% Palladium on carbon (250 mg) was added under an atmosphere of nitrogen to a solution of 4-(difluoromethyl)-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (2.5 g, 92.9 mmol) in methanol (25 mL). The flask was repeatedly evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to stir at rt for 2 h. The reaction vessel was purged with nitrogen gas. The crude reaction mixture was filtered through a short diatomaceous earth (Celite®) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. The crude product was purified using silica gel column chromatography (EtOAc/hexane) to afford 4-(4-(difluoromethyl)-1H-imidazol-1-yl)-3-methoxyaniline (1.8 g, 81% yield). LC-MS (M+H)+ 240.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (s, 1 H) 7.93 (s, 1 H) 7.47 (d, J=8.4 Hz, 1 H) 7.19-6.88 (m, 3 H) 3.81 (s, 3 H).

Provenance & Evidence