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

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

1. filtrationfiltered through celite
2. washwashed with EtOAc (20 mL×4)
3. washThe collected filtrate was further washed with brine (50 mL×3)
4. dry with materialdried over Na2SO4
5. customAfter removal of solvent
6. additionthe residue was diluted with MeOH (20 mL)
7. additionPd/C (50 mg, 5% mass equiv.) was added
8. additionthe reaction flask was charged with a H2 balloon
9. filtrationThe mixture was filtered through celite
10. washwashed with EtOAc (20 mL×3)
11. concentrationThe collected filtrate was concentrated
12. customthe residue was purified via flash chromatography (hexanes:EtOAc=1:1)

ORD record

ord-00dfce051fc5487cb5574f6d0be9d388

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889706B2