Toluene → HCID 67287030, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (51 mg, 0.1003 mmol), 3,4-dimethylphenylboronic acid (19.562 mg, 0.1304 mmol), sodium carbonate (31.901 mg, 0.301 mmol), toluene (1 mL), and water (0.1 mL) were placed in a vial with a Teflon lined screw cap. Argon was bubbled through the mixture for 10 minutes. Palladium (0) tetrakistriphenylphosphine (5.797 mg, 0.00501 mmol) was added and the vial was sealed. The vial was placed in a preheated sand bath (100° C.) and the mixture was stirred for 16 hours at that temperature. The mixture was cooled to ambient temperature and whole mixture was purified on silica gel (EtOAc-hexanes gradient) to provide 51.1 mg of the title compound as a thin film (95.5%).

Provenance & Evidence