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

Temperature

110 °C

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

ORD record

ord-18252121e59a4105926e1ff1b8c29cbe

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394818B2