Sodium Carbonate → N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Provenance & Evidence