Cesium fluoride → HCID 59187371, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-2′-fluoro-5′-methyl-3,3′-bipyridine-5-carboxylate (11-2, 0.098 g, 0.35 mmol, 1.0 equiv) in dimethylformamide (2.3 mL) was added 2-tri-n-butylstannylpyridine (0.26 g, 0.70 mmol, 2.0 equiv), cesium fluoride (0.16 g, 1.05 mmol, 3.0 equiv), copper (I) iodide (0.013 g, 0.070 mmol, 0.2 equiv), and tetrakis(triphenylphosphine)-palladium(0) (0.040 g, 0.035 mmol, 0.1 equiv) and the system was heated to 135° C. for 10 minutes in a microwave reactor. The reaction mixture was cooled and diluted with ethyl acetate (30 mL) and the reaction mixture was filtered through a pad of celite. The reaction mixture was washed with water (3×10 mL) and brine (1×10 mL), dried over magnesium sulfate and concentrated. The residue was purified via normal phase chromatography (10 to 100% EtOAc in hexanes, silica) to afford the desired product (11-3) as an oily solid after concentration. ESI+MS [M+H]+ C18H14FN3O2 calc'd 324.1. found 324.0.

Provenance & Evidence