Cesium carbonate → HCID 58424558, compound

Participants

Reaction Conditions

Reaction Steps

In a μwave vial was placed 6-bromo-4′-methoxyspiro[chroman-2,1′-cyclohexan]-4-one (48 mg, 0.148 mmol), 3-cyanobenzeneboronic acid (28 mg, 0.191 mmol), PdCl2(PPh3)2 (10 mg, 0.014 mmol) and cesium carbonate (121 mg, 0.371 mmol). This solid mixture was dissolved in a Dioxane/water mixture (2.0 mL, 6:1 ratio, respectively). The solution was purged with a N2 stream for 20 seconds. The vessel was placed in the μwave and heated to 100° C. for 5 minutes. After that time, the mixture was filtered through a Celite plug. The plug was rinsed with dichloromethane (10 mL) and water (10 mL). The phases in the filtrate were separated. The aqueous phase was back-extracted with dichloromethane (5 mL). The combined organic phases were washed with water, brine, dried over MgSO4, filtered and concentrated under reduce pressure. The crude material was purified by flash chromatography (ISCO, 12 g SiO2 cartridge, ethyl acetate/hexanes as the eluents). The corresponding fractions were combined and concentrated under reduce pressure yielding 3-(4′-methoxy-4-oxospiro[chroman-2,1′-cyclohexane]-6-yl)benzonitrile (32 mg, 0.092 mmol, 62% yield).

Provenance & Evidence