反应详情

To a mixture of N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide of Example 5 (0.466 g) in 15 mL diethylamine is added CuI (0.010 g) and (Ph3P)2PdCl2 (0.035 g). Propargyl alcohol (0.058 mL) is then added and the reaction is stirred overnight at room temperature. The diethylamine is removed in vacuo. The residue is partitioned between EtOAc and water. The insoluble material is filtered off and saved. The organic layer is washed with brine, dried and condensed. The residue is combined with the insoluble material and adsorbed onto silica and chromatographed, eluting with 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed to yield 0.192 g of the desired product as a tan solid.

1. customThe diethylamine is removed in vacuo
2. customThe residue is partitioned between EtOAc and water
3. filtrationThe insoluble material is filtered off
4. washThe organic layer is washed with brine
5. customdried
6. customcondensed
7. customchromatographed
8. washeluting with 3% MeOH/CH2Cl2
9. customcondensed