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

HRID 1431916

反応式

HRID 1431916 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

Isatin (0.12 g, 0.81 mmoles) 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 hour 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, pp. 5818-5827), (0.16 g, 0.47 mmoles) followed by copper iodide (0.32 g, 1.68 mmoles). 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).

後処理

  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

出典と根拠

ORDレコード
ord-e8c38ae8b92d4db39209a58e92cf0a14
出典データセット
uspto-grants-2009_11
特許番号
US07611909B1

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