Sodium Carbonate → HCID 89783120, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of compound 15 (1.5 g, 3.9 mmol) and 3-(methylsulfonyl)phenylboronic acid (1.2 g, 5.8 mmol) in DMF (10 mL) was degassed with argon. Tetrakis(triphenylphosphine)palladium(0) (450 mg, 0.3 mmol) was added and the reaction degassed for 30 min. Sodium carbonate (1.03 g, 9.0 mmol) was added to the reaction mixture, the reaction was degassed with argon for 30 min and heated to 90° C. for 3 h. Solvent was removed and the reaction mixture diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with saturated brine, dried over sodium sulphate and concentrated. The crude reaction mixture was purified by column chromatography using 30% ethyl acetate in hexane to afford 16 (1.2 g, 67%). LCMS: 459.20 (M+1)+; 1H NMR (DMSO-d6, 400 MHz) δ 8.13 (s, 1H), 8.05 (d, 1H, J=7.6 Hz), 7.91 (d, 1H, J=7.6 Hz), 7.82 (d, 1H, J=4 Hz), 7.75 (t, 2H, J=7.6 Hz) 7.20 (s, 1H), 5.40 (s, 2H), 4.01-4.23 (m, 2H), 3.32 (s, 3H), 1.1-1.25 (m, 3H).

Provenance & Evidence