Hydrochloric Acid → Methyl 4-(pyridin-4-yl)-1-naphthoate

Participants

Reaction Steps

A stirred solution of D7 (9.06 g, 26 mmole) in dry degassed DMF (150 ml) was treated with copper (I) iodide (495 mg, 2.6 mmole), dichlorobis(triphenylphosphine)palladium(II) (1.52 g, 2.2 mmole) and 4-bromopyridine (prepared by suspending the HCl salt (6.07 g, 31 mmole) in 40% KOH solution, extracting with toluene and adding the dried toluene solution to the reaction). The mixture was heated at reflux under argon for 5 h and allowed to cool before removing the DMF under vacuum. The residue was partitioned between EtOAc and 10% NaHCO3 solution and the organics dried (Na2SO4) and chromatographed on silica gel eluting with EtOAc to afford the title compound as a white solid (4.1 g, 60%).

Provenance & Evidence