Toluene → HCID 67520692, compound

Participants

Reaction Steps

A 2.5-5.0 mL microwave reaction tube was successively charged with 6 (200.0 mg, 0.43 mmol), trans-2-phenylvinylboronic acid (96.0 mg; 0.65 mmol), cesium carbonate (420.0 mg; 1.30 mmol), tetrakis(triphenylphosphine)palladium(0) (25.0 mg; 0.022 mmol), toluene (1.3 mL), ethanol (1.3 mL) and water (1.3 mL). The reaction tube was purged with nitrogen and subjected to the following microwave conditions: Temperature=140° C.; Power=250 W; Time=15 minutes; Cooling On; Absorption Very High. The reaction mixture was allowed to cool to room temperature and then was diluted with ethyl acetate (15 mL) and washed with aqueous hydrochloric acid (3×10 mL; 2N). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude dark oil residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution) to give the title product as a white solid (134 mg).

Provenance & Evidence