p-Fluoronitrobenzene → HCID 59285822, compound

Participants

Reaction Steps

Under ice-cooling, a solution of 2-aminocarbonylamino-5-(3-hydroxyphenyl)pyrrole-3-carboxamide (Compound No. 3-2, 100 mg, 0.38 mmol) in N,N-dimethylformamide (1.5 mL) was added to a suspension of 60% sodium hydride (23 mg, 0.58 mmol) in N,N-dimethylformamide (1.5 mL) and the mixture was stirred for 35 minutes. Moreover, 4-fluoronitrobenzene (61 μL, 0.57 mmol) was added thereto and the whole was stirred overnight at 50° C. Saturated aqueous ammonium chloride solution (3 mL) and water (3 mL) were added to the reaction solution, extracted with ethyl acetate (10 mL). The organic layer was washed with brine (10 mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (12 mg) as a yellow solid (Yield 8%).

Provenance & Evidence