反应详情

温度

95 °C

3,5-dichloropyridazine (200 mg, 1.34 mmol), 1-methyl-1H-indazole-5-boronic acid (260 mg, 1.48 mmol), K2CO3 (556.6 mg, 4.03 mmol), and tetrakis(triphenylphosphine)palladium(0) (233, 0.20 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (10 mL) and degassed water (2.5 mL). The reaction mixture was heated at 95° C. for 2 h then cooled to room temperature. The reaction mixture was filtered through Celite (ethyl acetate eluent) and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+: calc'd for C14H10ClN4: 245.1 (M+H+); Found: 245.2 (M+H+). 1H NMR (400 MHz, Chloroform-d) δ 9.15 (d, J=2.2 Hz, 1H), 8.44 (s, 1H), 8.21 (dd, J=8.8, 1.5 Hz, 1H), 8.11 (s, 1H), 7.97 (s, 1H), 7.56 (d, J=8.8 Hz, 1H), 4.14 (s, 3H).

1. customflushed with argon three times
2. additionTo this mixture was added
3. customdegassed 1,4-dioxane (10 mL)
4. customdegassed water (2.5 mL)
5. temperaturethen cooled to room temperature
6. filtrationThe reaction mixture was filtered through Celite (ethyl acetate eluent)
7. concentrationconcentrated
8. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
9. customprovided the product