Toluene → HCID 59118193, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of the compound of Example 203 (0.31 g, 0.49 mmol, 1.0 eq.) in toluene (1.0 mL) was added 4-methylphenylboronic acid (0.10 g, 0.73 mmol, 1.5 eq.), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.028 g, 0.034 mmol, 0.07 eq.) and 2M sodium carbonate (2.4 mL, 4.88 mmol, 10.0 eq.) under argon atmosphere at room temperature. The reaction mixture was allowed to heat up at 80° C. under argon atmosphere for 18 hours. The mixture was diluted with distilled water (3 mL) and extracted with diethyl ether (3×2 mL). The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was then treated with 4N hydrochloric acid (1.0 mL) in tetrahydrofuran (3 ml) and stirred at room temperature for 48 hours. The mixture was concentrated under reduced pressure to give white solid. Purification by HPLC followed yielded the desired product as clear oil (0.18 g, 77%). LC-MS: 578.0 (MH+), retention time: 4.63 min.

Provenance & Evidence