Ethyl Acetate → N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide

Participants

Reaction Conditions

Reaction Steps

N-(1-Adamantylmethyl)-2,5-dichloroisonicotinamide (2.32 g) and tributyl(vinyl)stannane (2.61 g) were stirred together in dry N,N-dimethylformamide (50 mL) at room temperature under nitrogen. The latter was treated with a few crystals of 2,6-ditert-butyl-4-methylphenol and dichloro[bis(triphenylphosphine)]palladium(II) (0.24 g). The reaction mixture was warmed to 80° C. for 4 hours and subsequently cooled to room temperature. The mixture was poured into ethyl acetate (50 mL) and washed with water (2×25 mL) then brine (30 mL). The organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (2.21 g).

Provenance & Evidence