Iodine → HCID 86663961, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 4-bromo-3-fluoro-2-nitro-6-(pyridin-2-yl)aniline (4.0 g, 12.81 mmol) in chloroform (50 mL) was added iodine (18.21 g, 71.77 mmol) and the resulting mixture was stirred at 0° C. for 10 min followed by addition of isoamyl nitrile (3.44 mL, 25.63 mmol). The mixture was then heated up to 65° C. for 5 h. After completion of reaction (by TLC), the reaction was diluted with 10% sodium bisulfite and extracted with DCM (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 20% EtOAc:hexane to obtain the desired product as an off white solid (2.0 g, 37%).

Provenance & Evidence