Potassium Carbonate → Ethyl 3-benzyl-2,4-dimethylquinoline-6-carboxylate

Participants

Reaction Steps

A mixture of ethyl 3-benzyl-2,4-dibromoquinoline-6-carboxylate (0.245 g, 0.545 mmol, Intermediate 34: step a), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.229 mL, 1.64 mmol), and 5 M aqueous K2CO3 (0.436 mL, 2.18 mmol) was treated with Pd(PPh3)4 (63 mg, 0.055 mmol) and dioxane (3 mL). This was microwaved under argon at 140° C. for 15 minutes (Biotage Initiator). The reaction was diluted with 1:1 heptane/EtOAc (5 mL), filtered, and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was flash chromatographed with a heptane to 70% EtOAc/heptane gradient to provide the title compound as a clear amber oil that crystallized upon standing.

Provenance & Evidence