Sodium Carbonate → 4-(2,6-Dimethylpyridin-3-yl)-1-naphthoic acid

Participants

Reaction Steps

A stirred mixture of D17 (0.32 g, 1.5 mmole), 3-bromo-2,6-dimethylpyridine hydrochloride (Synthesis 1974, 4, 293; 0.37 g, 1.6 mmole), Na2CO3 (0.48 g, 5.6 mmole) and tetrakis(triphenylphosphine)palladium (0) (0.08 g, 0.07 mmole) in 50% DME/water (20 ml) was heated at reflux under argon for 18 h. The mixture was concentrated in vacuo to 50% volume, diluted with water (20 ml), washed with EtOAc (2×10 ml), acidified with 2M HCl to pH 4 and extracted with DCM (3×25 ml). The combined extract was dried and evaporated to dryness. The residue was triturated in Et2O to afford the title compound as a buff powder (0.29 g, 69%).

Provenance & Evidence