反应详情

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and 3-phenylpropylamine (189 mg, 1.39 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (5 mL) of the crystals obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was dissolved in methanol (5 mL), and to this was added 1,1,1-trimethoxyethane (108 mg, 0.896 mmol), and this was heated to reflux for 6 hours. After the reaction was complete, this was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (58.5 mg, 14% yield) as white crystals.

1. temperaturethis was heated
2. temperatureto reflux for 3 hours
3. filtrationthe precipitated crystals were filtered
4. washwashed with water
5. customdried
6. customTo a tetrahydrofuran solution (5 mL) of the crystals obtained
7. filtrationthis was filtered through Celite
8. concentrationthe filtrate was concentrated
9. customThe residue obtained
10. temperaturethis was heated
11. temperatureto reflux for 6 hours
12. concentrationthis was concentrated
13. customthe residue obtained
14. customwas purified by silica gel column chromatography