反应详情

温度

100 °C

To a solution of 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]pyridine (i.e. the product of Example 13, Step A) (0.60 g, 1.95 mmol) in toluene (10 mL) was added benzyl bromide (0.670 g, 3.90 mmol), and the reaction mixture was heated to 100° C. for 12 h. Then the reaction mixture was cooled to room temperature. The solid that precipitated out was filtered and dried. The solid was dissolved in methanol (10 mL), and sodium borohydride (0.072 g, 1.95 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 h, diluted with water (50 mL), neutralized with 1.5 N aqueous hydrochloric acid solution, and extracted with ethyl acetate (50 mL). The organic layer was separated, washed with brine (25 mL), and concentrated under reduced pressure. The residue was purified by medium-pressure liquid chromatography using 3% of methanol in chloroform as eluant to give 0.4 g of the title compound as a white solid.

1. temperatureThen the reaction mixture was cooled to room temperature
2. customThe solid that precipitated out
3. filtrationwas filtered
4. customdried
5. dissolutionThe solid was dissolved in methanol (10 mL)
6. extractionextracted with ethyl acetate (50 mL)
7. customThe organic layer was separated
8. washwashed with brine (25 mL)
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by medium-pressure liquid chromatography