Potassium Carbonate → 6-methyl-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Participants

Reaction Conditions

Reaction Steps

6-bromo-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (10 mg, 0.027 mmol), trimethylboroxine (10 μL, 0.071 mmol), tetrakis(triphenylphosphine)palladium (0) (5 mg, 0.004 mmol), and potassium carbonate (15 mg, 0.108 mmol) were combined in a dry flask. The flask was purged with argon and 0.5 mL of 10% aqueous dioxane were added. Argon was bubbled through the solution for 5 minutes and the solution was stirred and heated to 100° C. After 12 hours, the reaction mixture was filtered through a pad of Celite, eluted with EtOAc, washed with brine, dried over sodium sulfate, filtered, concentrated and purified by reverse phase HPLC (30-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 9.11 (d, 1H), 8.54 (d, 1H), 7.80 (d, 2H), 7.54 (m, 5H), 7.48 (m, 2H), 7.26 (d, 2H), 2.56 (s, 3H). LRMS (APCI) calculated for C21H16NO [M+H]+, 298.1; found 298.1.

Provenance & Evidence