Dichloromethane → HCID 68379983, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-3-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]pyrido[2,3-h]quinazolin-4(3H)-one (1.00 g, 2.66 mmol) in 6 mL of DMF under an atmosphere of nitrogen was added potassium acetate (0.783 g, 7.97 mmol), bis(pinacolato)diboron (1.01 g, 3.99 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (0.217 g, 0.266 mmol). The mixture was heated at 80° C. for 2 h, cooled to rt, and treated with 1 N aqueous sodium hydroxide to pH ˜9. The aqueous solution was washed 2× with dichloromethane, then treated with 10% aqueous potassium phosphate to pH ˜7. A brown solid was collected via filtration to provide {3-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-4-oxo-3,4-dihyrdopyrido[2,3-h]quinazolin-6-yl}boronic acid that gave a mass ion (ES+) of 342.0 for [M+H]+.

Provenance & Evidence