2-Methoxyethylamine → Methyl 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylate

Participants

Reaction Conditions

Reaction Steps

Freshly purified cesium carbonate (1.4 eq.), palladium(II) acetate (0.02 eq.) and rac-BINAP (0.03 eq.) were combined in anhydrous toluene (0.25 M). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, methyl 3-bromo-1-naphthalenecarboxylate (1 eq.) and 2-methoxyethylamine (1.2 eq.) were added and the resulting mixture was heated at 100° C. for 20 h. The now black suspension was cooled to RT, diluted with ether and filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a brown oil that can be purified further by way of column chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) to afford the title compound as a yellow oil.

Provenance & Evidence