Tetrahydrofuran → HCID 11335358, compound

Participants

Reaction Steps

To a stirred solution of 4-(6-bromo-pyridin-2-ylmethyl)-1,4-diaza-bicyclo[3.2.2]nonane (17.0 mg, 0.06 mmol) in a solvent mixture of THF, ethanol, and water (6.0 mL of 1:1:1) was added phenylboronic acid (18 mg, 0.15 mmol), potassium carbonate (70 mg), and a catalytic amount of tetrakis(triphenylphosphine)palladium(0). The mixture was heated at reflux temperature for 3 hours, cooled, and concentrated to near dryness. The residue was triturated with chloroform (3×) and the crude product in chloroform subjected silica gel chromatography eluting with a chloroform (ammoniated) to 5% methanollchloroform gradient to give the title compound as an off-white solid (4.8 mg). MS (ES+) 294 (MH+).

Provenance & Evidence