Sodium Carbonate → HCID 71263274, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-quinuclidin-3-yl((3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromophenyl)(phenyl)methyl)carbamate (0.2 g, 0.33 mmol) (prepared in Example 28 Step 8) in toluene (4 mL) and water (1 mL), was added phenyl boronic acid (0.04 g, 0.33 mmol), sodium carbonate (0.07 g, 0.66 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.04 g, 0.03 mmol). The reaction mixture was heated in the microwave at 120° C. for 30 minutes. The solvent was removed under reduced pressure, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were dried (sodium sulphate), filtered and solvent removed under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.14 g, 71%).

Provenance & Evidence