反应详情

To a mixture of 7-bromo-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Example 5e) (180 mg, 0.57 mmol) in dimethoxyethane (DME) (2.5 mL) was added 4-methoxyphenylboronic acid (104 mg, 0.69 mmol), Pd(PPh3)4 solid (66 mg, 0.06 mmol) and then 2M aqueous Na2CO3 solution (0.7 mL). The resulting mixture was purged with nitrogen gas for 1 min and heated to reflux for 2 h. After cooling the reaction mixture was diluted with water (50 mL) and acidified using 1 N HCl to pH 3-4. The precipitate was collected by filtration, rinsed with water and dissolved in CH2Cl2. The organic solution was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was triturated with MeOH (5 mL) and the solid collected, rinsed with MeOH (2 mL) and dried in vacuo to provide 4-hydroxy-7-(4-methoxy-phenyl)-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (139 mg). MS ESI(+) m/e: 343.11 (M+1).

1. customThe resulting mixture was purged with nitrogen gas for 1 min
2. temperatureheated
3. temperatureto reflux for 2 h
4. temperatureAfter cooling the reaction mixture
5. additionwas diluted with water (50 mL)
6. filtrationThe precipitate was collected by filtration
7. washrinsed with water
8. dissolutiondissolved in CH2Cl2
9. washThe organic solution was washed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product was triturated with MeOH (5 mL)
14. customthe solid collected
15. washrinsed with MeOH (2 mL)
16. customdried in vacuo