Sodium Carbonate → HCID 19045053, compound

Participants

Reaction Steps

To a solution of the title compound of Step E (1.65 g, 5.73 mmol) in ethylene glycol dimethyl ether (25 mL) was added the title compound of Step F (1.73 g, 8.59 mmol), a solution of sodium carbonate (1.82 g, 17.2 mmol) in water (15 mL) and bis(triphenylphosphine) palladium (II) chloride (201 mg, 0.286 mmol). The mixture was heated at reflux overnight, then cooled to room temperature and poured into water. The mixture was extracted twice with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to give a dark-brown oil. Flash chromatography of this oil on silica gel eluting with 1:25 ethyl acetate/hexane afforded the title compound of Step G, a compound of the invention, as light-yellow solid melting at 154°-155° C. (525 mg, 25%). 1H NMR (CDCl3): δ2.64 (s,3H), 7.15-7.25 (m,3H), 7.39 (t, 1H), 7.7 (s, 1H), 7.97 (s, 1H), 8.62 (s, 1H).

Provenance & Evidence