تفاعل #6704

معادلة التفاعل

Isatin

sodium hydride

4-(3-bromophenyl)phenol benzyl ether

→

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

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر