Lithium Chloride → HCID 57485796, compound

Participants

Reaction Steps

A mixture of ethyl 6-trifluoromethanesulfonyloxy-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate (270 mg, 0.790 mmol) in 6 mL of dimethoxyethane, 1.5 mL of saturated sodium carbonate solution, 3-pyridineboronic acid (146 mg, 1.20 mmol) and lithium chloride (99 mg, 2.37 mmol) was degassed and placed under an argon atmosphere (5 min purge). Tetrakis(triphenyphosphine)palladium(0) (60 mg) was added, and the reaction mixture was heated at reflux for 4 h. It was then cooled and filtered though a plug of silica gel, eluting with ethyl acetate. Concentration of the filtrate and column chromatography of the residue, with a gradient of 0-5% methanol in dichloromethane, gave a yellow oil (130 mg, 60%).

Provenance & Evidence