反应详情

温度

90 °C

A mixture of 4-iodo-5-methyl-3-phenylisoxazole (285 mg, 1.00 mmol), palladium(II) acetate (7 mg, 0.03 mmol), 1,3-bis(diphenylphosphino)propane (12 mg, 0.03 mmol), triethylamine (348 μL, 2.50 mmol) and 2-ethynylpyridine (131 μL, 1.30 mmol) in N,N-dimethylformamide (2 mL) was evaporated and flushed with argon. Cuprous iodide (4 mg, 0.02 mmol) was added and the reaction mixture was stirred for 3 h at 90° C. before cooling to ambient temperature and separated between aqueous sodium hydroxide (1 M, 30 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and washed with aqueous sodium hydroxide (1 M, 30 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33) afforded the title compound (60 mg, 23%) as a light brown solid. MS: m/e=261.2 [M+H]+.

1. customwas evaporated
2. customflushed with argon
3. temperaturebefore cooling to ambient temperature
4. customseparated between aqueous sodium hydroxide (1 M, 30 mL) and ethyl acetate (50 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
6. washwashed with aqueous sodium hydroxide (1 M, 30 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. concentrationconcentrated
9. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33)