Water → 5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.16 g, 0.41 mmol) and (2-fluorophenyl)boronic acid (0.069 g, 0.49 mmol) in 1,4-dioxane (2 mL) was added 1 N solution of sodium carbonate in water (0.62 mL, 34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.020 mmol). The mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and then concentrated. The residue was purified on silica gel (eluting with 0-60% EtOAc in Hexane) to give the desired compound as a bis-trifluoroacetate salt (42 mg, 29%). LCMS calculated for C18H15ClFN2O2(M+H)+: m/z=345.1; found: 345.0.

Provenance & Evidence