Dimethylformamide → HCID 68822450, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing 13.1 (1.75 g, 7.01 mmol), 2-fluoro-5-methoxyphenylboronic acid (2.0 g, 11.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.81 g, 0.70 mmol), and potassium carbonate (2.91 g, 21.0 mmol) was added a premixed 3:1 solution of toluene (18 mL) and DMF (6 mL, 7.01 mmol). The mixture was heated at 100° C. and monitored with TLC. After 17 hours, the reaction was cooled to room temperature then partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc (2×20 mL). The organic layers were combined, washed with brine, and dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtering, and the organic phase was concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes) to yield a colorless oil 13.2 (1.01 g, 49% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 8.04 (1H, m), 8.02 (1H, m) 7.57 (1H, d, J=8.2 Hz), 7.09 (1H, t, J=9.0 Hz), 6.93 (1H, dt, J=9.0, 3.5 Hz), 6.82 (1H, dd, J=5.1, 3.1 Hz), 3.93 (3H, s), 3.83 (3H, s).

Provenance & Evidence