Reaction #6704

Reaction equation

Isatin

sodium hydride

4-(3-bromophenyl)phenol benzyl ether

→

N-[3-(4-benzyloxyphenyl)phenyl]isatin

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureThe reaction was heated in an oil-bath at 140° C
2. 2
   workup.WAITAfter ˜16 hours
3. 3
   Temperaturethe reaction was cooled to room temperature
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (˜75 mL)
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   Otherto afford a sticky, brown solid which
9. 9
   Otherwas purified by preparative TLC on silica gel using 25% ethyl acetate in hexanes as the developing solvent

Procedure

Isatin (0.12 g, 0.81 mmol) in anhydrous DMF (30 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (21 mg, 1.1 equivalents). The reaction was stirred in ice for 0.5 hours and then warmed to room temperature. This solution was then treated with 4-(3-bromophenyl)phenol benzyl ether (Hajduk et al. J. Am. Chem. Soc. 1997, 119, 5818–5827), (0.16 g, 0.47 mmol) followed by copper iodide (0.32 g, 1.68 mmol). The reaction was heated in an oil-bath at 140° C. After ˜16 hours, the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (˜75 mL) and filtered. The filtrate was concentrated under reduced pressure to afford a sticky, brown solid which was purified by preparative TLC on silica gel using 25% ethyl acetate in hexanes as the developing solvent. Rf (product)=0.38. Yield=47 mg (25%); MALDI-TOF MS 407.02 obs. (405.5 calc.); 1H-NMR (CDCl3) 5.12 (s, 2H), 6.95 (d, 1H, J=8 Hz), 7.06 (d, 2H, J=8.8 Hz), 7.18 (t, 1H, J=7.5 Hz), 7.33–7.47 (m, 7H), 7.53 (d, 2H, J=8.8 Hz), 7.57–7.60 (m, 2H), 7.71 (d, 1H, J=7.5 Hz).

Source