反应详情

温度

60 °C

To a solution of Intermediate 1 (509 mg, 1.32 mmol) in N,N-dimethylformamide (5 mL) was added 4-chloromethyl-2-methyl-oxazole from Step A (173 mg, 1.32 mmol), potassium carbonate (273 mg, 1.98 mmol) and 18-crown-6 (40 mg). The slurry was heated at 60° C. for eighteen hours. The reaction was allowed to cool to room temperature and then partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the title compound as a colorless oil. (160 mg, 25% yield). MS (M+H): 482; 1H NMR (400 MHz, chloroform-d) δ ppm, 1.64 (s, 6H), 2.17 (s, 3H), 2.20 (s, 3H), 2.50 (s, 3H), 5.40-5.48 (m, 2H), 7.54-7.58 (m, 2H), 7.66 (s, 1H), 7.93 (s, 1H), 8.13 (d, J=8.21 Hz, 1H), 8.77 (d, J=5.08, 1H).

1. temperatureto cool to room temperature
2. custompartitioned between ethyl acetate and water
3. washThe organic layer was washed with water and brine
4. dry with materialdried over magnesium sulfate
5. filtrationThe slurry was filtered
6. concentrationconcentrated in vacuo
7. customThe crude material was purified