反应详情

温度

90 °C

A mixture of 4-ethynyl-5-methyl-3-phenyl-isoxazole (110 mg, 0.60 mmol), 2-chloro-4-iodopyridine (172 mg, 0.72 mmol), triethylamine (209 μl, 1.50 mmol) and bis(triphenylphosphine)palladium(II) chloride (13 mg, 0.02 mmol) in N,N-dimethylformamide (1.2 mL) was evaporated and flushed with argon. Cuprous iodide (2 mg, 0.01 mmol) was added and the reaction mixture was stirred for 1.5 h at 90° C. before it was cooled to ambient temperature and separated between aqueous sodium hydroxide (1 M, 20 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (30 mL) and the combined organic layers were washed with aqueous sodium hydroxide (1 M, 20 mL), dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (160 mg, 91%) as a colorless oil. MS: m/e=295.0/297.2 [M+H]+.

1. customwas evaporated
2. customflushed with argon
3. temperaturewas cooled to ambient temperature
4. customseparated between aqueous sodium hydroxide (1 M, 20 mL) and ethyl acetate (30 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (30 mL)
6. washthe combined organic layers were washed with aqueous sodium hydroxide (1 M, 20 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)