4-Bromonaphth-1-ylacetic acid (J. Org. Chem., 1951, 16, 1588) (1 g, 3.78 mmole) in 1,2-dimethoxyethane (50 ml) was treated with pyridin-4-ylboronic acid (465 mg, 3.78 mmole), sodium hydrogen carbonate (952 mg, 11.3 mmole) and water (10 ml). A stream of argon was bubbled through the mixture for 15 minutes, then tetrakis(triphenylphosphine)palladium (0) (200 mg 0.17 mmole) was added and the mixture heated under reflux for 18 hours. The mixture was then concentrated in vacuo to a gum, which was partitioned between 2M sodium hydroxide solution and dichloromethane. The aqueous layer was separated, adjusted to pH 0 with 6M hydrochloric acid and washed with dichloromethane; then adjusted to pH 7 by addition of aqueous potassium carbonate solution and extracted with dichloromethane. The dichloromethane extract was dried (Na2SO4) and concentrated in vacuo to give the title compound, which crystallised from ether as needles mp 210-215° C. (465 mg, 46%).
