Potassium Phosphate, Tribasic → HCID 57672419, compound

Participants

Reaction Steps

To a round bottom flask containing 13.2 (0.46 g, 1.56 mmol), cyclopropylboronic acid (0.40 g, 4.67 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.26 g, 0.638 mmol), palladium acetate (0.07 g, 0.31 mmol), and potassium phosphate tribasic (1.00 g, 4.71 mmol), was added a premixed solution of 1,4-dioxane (1.0 mL) and water (0.3 mL). The mixture was stirred at room temperature for 5 minutes and then heated to 88° C. and monitored with TLC. After 4 hours, the reaction was cooled to room temperature and diluted with EtOAc. The mixture was then filtered through a pad of silica gel (eluting with EtOAc) and concentrated under reduced pressure. The crude residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 25% EtOAc in hexanes) to yield a colorless oil 13.3 (0.4 g, 85% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, m), 7.07 (1H, t, J=8.8 Hz), 6.96 (1H, d, J=8.2 Hz), 6.91 (2H, m), 3.89 (3H, s), 3.81 (3H, s), 1.84 (1H, dt, J=8.6, 4.3 Hz), 0.93 (2H, m), 0.75 (2H, m).

Provenance & Evidence