反应详情

温度

140 °C

A suspension of 8-bromo-2-(5-isopropyl-[1,2,4]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (84 mg, 0.21 mmol), 4,4,5,5-tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (62 mg, 0.32 mmol), tetrakis(triphenylphosphine) palladium (0) (24 mg, 0.021 mmol) and sodium carbonate (45 mg, 0.42 mmol) in acetonitrile (6 mL) and water (3 mL) under nitrogen was heated at 140° C. for 25 mins under microwave irradiation. More tetrakis(triphenylphosphine) palladium (0) (24 mg, 0.021 mmol) was added, and heating was pursued for 30 mins at 150° C. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo and purified twice by flash chromatography (SiO2, gradient 50 to 75% ethyl acetate in cyclohexane, then 60% ethyl acetate in cyclohexane) to afford 484 as an off-white solid (16 mg, 20%). LCMS (Method C): RT=10.30 min, [M+H]+=379. 1H NMR (DMSO-d6): 12.98 (1 H, bs), 8.28 (1 H, bs), 8.18 (1 H, d, J=8.3 Hz), 8.16 (1 H, s), 7.99 (1 H, bs), 7.46 (1 H, dd, J=8.3, 1.8 Hz), 7.34 (1 H, d, J=1.8 Hz), 4.38 (2 H, t, J=5.0 Hz), 4.13-4.01 (1 H, m), 3.37 (2 H, t, J=5.0 Hz), 1.43 (3 H, s), 1.41 (3 H, s).

1. temperatureheating
2. washThe organic layer was washed with brine
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. custompurified twice by flash chromatography (SiO2, gradient 50 to 75% ethyl acetate in cyclohexane