反应详情

温度

85 °C

A solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde (200 mg, 1.26 mmol), sodium carbonate (282 mg, 2.66 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (426 mg, 1.64 mmol) and palladium tetrakis(triphenylphosphine) (73 mg, 0.063 mmol) in a mixture of dimethoxyethane (4 mL) and water (1.35 mL) was heated at 85° C. for 24 hours. After cooling to room temperature, the mixture was poured into water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20 then 50/50) to provide the desired product (27a) (110 mg, 0.43 mmol, 34%) as a beige solid.

1. temperatureAfter cooling to room temperature
2. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
3. washThe organic layer was washed with brine (10 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20