Water → HCID 89649331, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-bromo-5-tert-butoxy-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 36) (605 mg, 1.59 mmol) in 1,2-dimethoxyethane (16 mL) was added water (4 mL), [4-(trifluoromethyl)phenyl]boronic acid (332.38 mg, 1.75 mmol) and sodium carbonate (505.87 mg, 4.77 mmol). The mixture was degassed with a stream of nitrogen and bis(triphenylphosphine)-palladium (II) dichloride (55.83 mg, 0.0800 mmol) was added. The mixture was heated to 120° C. over 15 minutes in a microwave. The reaction mixture was diluted with DCM and a little water and the phases separated with a hydrophobic frit. The organic filtrate was evaporated to yield a brown gum, (798 mg). Column chromatography (0-10% MeOH in EtOAc) yielded 2-[5-tert-butoxy-4-[4-(trifluoro-methyl)-phenyl]-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (263 mg, 0.5904 mmol, 37.1% yield) as a yellow foam;

Provenance & Evidence