Sodium Carbonate → HCID 18439657, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound of Example 100 (250 mg, 0.57 mmol), 4-cyanophenyl boronic acid (108 mg, 0.74 mmol), 2M aqueous sodium carbonate solution (0.5 mL, 1.0 mmol), and (bistriphenylphosphine)palladium(II) chloride (50 mg, 0.071 mmol) was suspended in DMF (2 mL) and stirred at 100° C. After 20 min, the reaction was determined to be complete by TLC analysis. After cooling to RT, the DMF was evaporated under reduced pressure. The crude product was partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (1:1) to afford the title compound (152 mg, 58%) as a solid white powder. 1H NMR (400 MHz, d6-DMSO): δ 9.82 (s, 1H), 8.81 (d, J=2.2, 1H), 7.95–8.05 (m, 5H), 7.68–7.74 (m, 3H), 7.63 (d, J=7.8, 1H), 7.53 (dd, J1=2.2, J2=8.7, 1H), 7.31 (d, J=8.5, 1H), 4.01 (s, 3H), 3.24 (q, J=7.3, 2H), 1.14 (t, J=7.3, 3H). MS (ES+, m/z)=459 (m+H)+.

Provenance & Evidence