N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide → N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

Participants

Reaction Steps

Bromo(3-cyanopropyl)-zinc (30 mL, 0.5 M in tetrahydrofuran) and tetrakis(triphenylphosphine)palladium(0) (86 mg) were added to N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (500 mg). The reaction mixture was heated to reflux for 30 minutes. The mixture was cooled to room temperature and then poured into aqueous saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried, filtered and evaporated. Purification (SiO2, methanol:dichloromethane 3:97 as eluant) gave the sub-title compound as a solid (490 mg).

Provenance & Evidence