Sodium Bicarbonate → HCID 66666740, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-4-phenoxybenzonitrile (Preparation 21, 0.21 g, 0.7 mmol), (2-methoxypyridin-3-yl)boronic acid (0.2 g, 1.1 mmol) and sodium hydrogen carbonate (0.19 g, 2.1 mmol) was suspended in dioxane (10 mL) and water (3 mL). The reaction mixture was degassed for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.050 g, 0.07 mmol) was added and the mixture heated at 100° C. for 1 hour. After the reaction was allowed to cool to room temperature, the reaction was partitioned between EtOAc (50 mL) and water (15 mL). The organic layer was filtered through a pad of celite and the solvent removed in vacuo to provide a crude brown solid. The crude material was purified by silica gel chromatography eluting with 30% EtOAc in Heptane to afford the title compound as a yellow solid (0.23 g).

Provenance & Evidence