反应详情

2-Bromo-N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dlhydrofuro[2,3-b]-pyridine-5-carboxamide (Example 79, 0.593 g) was suspended in a mixture of triethylamine (15 mL) and DMF (3 mL). CuI (0.029 g), Pd(PPh3)2Cl2 (0.105 g), and then 1-phenyl-3-butyn-1-ol (0.36 mL) were added. The reaction mixture was stirred at room temperature for 20 min and then was partitioned between CH2Cl2 (50 mL) and water (50 mL). The aqueous layer was separated and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with a sat. aq. ammonium chloride solution (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from methanol to yield 0.275 g of the title compound as a yellow solid. Physical characteristics. M.p. 202-203° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.50, 8.58, 7.44-7.25, 7.15, 5.73, 4.85-4.81, 4.55, 3.91, 2.89; MS (ESI+) m/z 461 (M+H)+.

1. customwas partitioned between CH2Cl2 (50 mL) and water (50 mL)
2. customThe aqueous layer was separated
3. extractionextracted with CH2Cl2 (3×50 mL)
4. washThe combined organic layers were washed with a sat. aq. ammonium chloride solution (100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
9. customfollowed by recrystallization from methanol