Sodium Carbonate → HCID 89649221, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5S)-2-(4-bromo-2-pyridyl)-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 19) (200 mg, 0.6800 mmol) in 1,2-dimethoxyethane (3 mL) and water (1 mL) was added [4-(trifluoromethyl)phenyl]-boronic acid (142.05 mg, 0.7500 mmol) and sodium carbonate (216.2 mg, 2.04 mmol). The reaction mixture was degassed with nitrogen and then treated with bis(triphenylphosphine)palladium (II) dichloride (23.86 mg, 0.0300 mmol). The reaction mixture was heated in the microwave at 120° C. for 50 minutes then cooled and diluted with dichloromethane and water. After separation of the layers, the aqueous phase was re-extracted with dichloromethane and the combined organic phases passed through a hydrophobic frit. The solvent was evaporated and the residue purified by silica gel chromatography eluting with 0-20% methanol in ethyl acetate to give (5S)-2-[4-[4-(trifluoromethyl)-phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (D20) as a pale yellow solid (181 mg);

Provenance & Evidence