反应详情

To a solution of 5-chlorooxindole (0.629 g, 3.78 mmol) in 10.0 mL monoglyme was added 7.51 mL sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring a troom temperature for 8 min, a solution of 5-aminophthalide (0.561 g, 3.78 mmol) in 3.0 mL of DMF was added over 1 min. The mixture was stirred for 40 min and then quenched into 4% aqueous HCl solution. The aqueous solution was neutralized to pH 7 with 1 M NaOH and then made basic with saturated NaHCO3. The solid was filtered and washed with H2O and then partitioned between EtOAc and saturated NaHCO3 (heated to dissolve the solid). The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue triturated with MeOH to give the title compound (353 mg, 31%) as a yellow solid.

1. stirringThe mixture was stirred for 40 min
2. customquenched into 4% aqueous HCl solution
3. filtrationThe solid was filtered
4. washwashed with H2O
5. custompartitioned between EtOAc and saturated NaHCO3 (
6. temperatureheated
7. dissolutionto dissolve the solid)
8. washThe organic phase was washed with H2O, brine
9. dry with materialdried with Na2SO4
10. customThe solvent was removed in vacuo
11. customthe residue triturated with MeOH