Potassium Carbonate → HCID 25263858, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 9-bromo-2-methyl-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (0.1 g, 0.31 mmol) in 1,4-dioxane (1.0 mL) was added phenylboronic acid (0.056 g, 0.459 mmol), potassium carbonate (0.118 g, 0.857 mmol) and 1,1′-bis[di(t-butylphosphine)ferrocene]PdCl (0.02 g, 0.031 mmol). The reaction mixture was heated at 90° C. for 6 hours. The resulting mixture was filtered and solvent removed under reduced pressure. The crude mixture was purified by flash column chromatography (SiO2, 16% EtOAc in hexanes) to give the product as a purple solid (0.024 g, 20%). M.p.=190-192° C.; 400 MHz 1H NMR (CDCl3) δ: 8.11 (d, J=7.6, 1H), 7.93 (d, J=1.6, 1H), 7.66 (m, 3H), 7.45 (m, 3H), 4.70 (m, 1H), 3.11 (d, J=13.2, 1H), 2.94 (m, 1H), 1.65 (m, 3H); LCMS: 323 [M+H].

Provenance & Evidence