Triethylamine → Methyl quinoline-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of quinolin-7-yl trifluoroacetate (750 mg, 2.7 mmol), PdCl2(Ph3P) (95 mg, 0.14 mmol), and triethylamine (1.2 mL, 8.4 mmol) in 1:2 DMF/MeOH (39 mL) was degassed and sparged with CO, and the mixture was heated at 60° C. for 48 h. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. The residue was diluted with a 5% solution of LiCl, and washed with CHCl3 (3×250 mL). The combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes) provided methyl quinoline-7-carboxylate (185 mg): ESI MS m/z 188 [M+H]+.

Provenance & Evidence