Ammonium Chloride → 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-1-benzothiophen-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 1407527노트

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HRID 1407527 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:2]1=2.C([Mg]Cl)(C)C.[C:16]1([CH:22]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[C:24]2=[O:33])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1.ClCCCl>[C:34]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([OH:32])([C:8]3[C:7]([OH:10])=[CH:6][C:3]4[CH:4]=[CH:5][S:1][C:2]=4[CH:9]=3)[C:24]2=[O:33])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 12203499Benzo[b]thiophen-5-olHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 685980971-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-1-benzothiophen-6-yl)-1,3-dihydro-2H-indol-2-one수율 59.3%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매2회

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온도
5 °C

실험 절차

To a solution of benzo[b]thiophen-5-ol (1.39 g, 9.25 mmol) in tetrahydrofuran (50 mL) at 5° C. was added a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (5.0 mL, 10 mmol). The reaction mixture was stirred at 5° C. for 15 min and concentrated in vacuo. To the residue were added 1,2-dichloroethane (100 mL) and 1-(diphenylmethyl)-1H-indole-2,3-dione (2.5 g, 8.0 mmol). The reaction mixture was heated at reflux for 3 h, allowed to cool to ambient temperature and stirred for 48 h. Saturated aqueous ammonium chloride (10 mL) was added and the phases were separated. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with a 0% to 20% gradient of ethyl acetate in dichloromethane to afford 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-1-benzothiophen-6-yl)-1,3-dihydro-2H-indol-2-one (2.2 g, 59%) as an off-white solid: MS (ES+) m/z 486.0 (M+23).

후처리

  1. concentrationconcentrated in vacuo
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 3 h
  4. temperatureto cool to ambient temperature
  5. stirringstirred for 48 h
  6. customthe phases were separated
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography
  11. washeluted with a 0% to 20% gradient of ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-d017f64776b94a64a28d5056ce6aa027
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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