N,N'-Dimethylethylenediamine → Acetamide, N-(4-cyano-2-fluorophenyl)-

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (137 mg, 2.796 mmol) dried KI (77 mg, 0.464 mmol, 20 mol %) and CuI (44 mg, 0.231 mmol, 10 mol %), N-(4-Bromo-2-fluoro-phenyl)-acetamide (540 mg, 2.330 mmol), evacuated and backfilled with argon three times. Anhydrous toluene (1.550 mL) and N,N′-dimethylethylenediamine (250 μl, 2.348 mmol) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow color suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide 30% and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The organic layers combined were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 372 mg (90% yield) of the title compound as a pale yellow solid.

Provenance & Evidence