Ethyl Acetate → 6-Acetyl-3-fluoro-5,6-dihydro-2-(6-methoxy-3-pyridinyl)-pyrido[3,2-c][1]benzazocine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1D (20 mg, 0.066 mmol) in toluene (0.5 mL) and EtOH (0.3 mL) was added a 2M aqueous solution of Na2CO3 (0.3 mL, 0.6 mmol). The resulting solution was purged with argon for 30 minutes and 2A (23.3 mg, 0.099 mmol) was added, followed by a catalytic amount of Pd(PPh3)4. The reaction was heated to 100° C. for 15 minutes, then cooled to ambient temperature. EtOAc and H2O were added, the layers were separated and the organic phase was washed with saturated aqueous NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 100% CH2Cl2 then 100% EtOAc) to afford 2B (23.7 mg, 96%). HPLC Rt=3.182 min; LCMS Found: (M+H)+=376.

Provenance & Evidence