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

HRID 6608

반응식

HRID 6608 반응식
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30](Br)[CH:29]=2)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.[Cu](I)I>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[C:30]([N:1]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4](=[O:5])[C:2]3=[O:3])[CH:31]=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 186833604-(3-Bromophenyl)phenol benzyl ether

생성물 1

HCID 22016446N-[3-(4-benzyloxyphenyl)phenyl]isatin

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  1. temperatureThe reaction was heated in an oil-bath at 140° C
  2. waitAfter ˜16 hours
  3. temperaturethe reaction was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (˜75 mL)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto afford a sticky, brown solid which
  9. customwas purified by preparative TLC on silica gel using 25% ethyl acetate in hexanes as the developing solvent

출처 및 근거

ORD 기록
ord-9d1d916dbb9740ceb7e832ab900fa980
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083986B2

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