Acetate → HCID 89781946, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Pd(PPh3)4 (608 mg, 0.53 mmol), tributyl(1-ethoxyvinyl)tin (3.91 mL, 11.57 mmol), methyl 8-bromoquinoline-2-carboxylate (2.80 g, 10.52 mmol), and toluene (50 mL) was heated under argon at 100° C. for 18 h. The mixture was then concentrated under reduced pressure and adsorbed onto silica gel. Column chromatography (silica gel, 10-100% EtOAc in hexanes) afforded a mixture of vinyl ether (M+1=258.0) and the desired acetate. This mixture was dissolved in THF (40 mL), the solution was cooled to 0° C., 10 drops of 1N HCl were added, and the solution was stirred at 0° C. for 5 min. EtOAc (100 mL) was added and the resulting solution was washed successively with 1N NaOH (20 mL), water (40 mL) and brine (40 mL). Significant product remained in the aq. layer and was extracted with 25% IPA in CHCl3. The combined organic layers were dried over MgSO4, filtered, and concentrated to give methyl 8-acetylquinoline-2-carboxylate (1.98 g, 8.64 mmol, 82% yield) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (d, J=8.4 Hz, 1H), 8.27 (dd, J=8.2, 1.4 Hz, 1H), 8.20 (d, J=8.4 Hz, 1H), 8.00 (dd, J=7.2, 1.4 Hz, 1H), 7.79-7.86 (m, 1H), 3.98 (s, 3H), 2.92 (s, 3H). m/z (ESI, +ve ion) 230.0 (M+H)+.

Provenance & Evidence