Sodium Carbonate → N-({3-Chloro-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)cyclopropanamine

Participants

Reaction Conditions

Reaction Steps

To a 4:1 (v/v) DMF:n-propanol solution (0.15 M) of N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (2 eq.) was added trans-dibromobis(triphenylphosphine) palladium(II) (0.05 eq.) followed by sodium carbonate (2 M aqueous solution, 3 eq.). The reaction vessel was evacuated and purged with nitrogen five times and then heated at 100° C. for 2 h. The cooled reaction mixture was poured into aq. sat. NH4Cl and then extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:7 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as an oil.

Provenance & Evidence