Ammonium Chloride → 1-(diphenylmethyl)-3-(5-fluoro-7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

HRID 1407523노트

반응식

HRID 1407523 반응식
[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([OH:12])[CH:3]=1.C([Mg]Cl)(C)C.[C:18]1([CH:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:34])[C:26]2=[O:35])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>ClCCl.O1CCCC1>[C:36]1([CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([C:3]3[C:4]([OH:12])=[CH:5][C:6]4[O:11][CH2:10][CH2:9][O:8][C:7]=4[C:2]=3[F:1])([OH:34])[C:26]2=[O:35])[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 673575678-Fluoro-2,3-dihydro-1,4-benzodioxin-6-olHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 673575191-(diphenylmethyl)-3-(5-fluoro-7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-3-hydroxy-1,3-dihydro-2H-indol-2-one수율 64%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A 100 mL round-bottom flask was charged with 8-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-ol (6.4 g, 37 mmol) and tetrahydrofuran (60 mL). A 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (20.0 mL, 40.0 mmol) was added at 5° C. and the reaction mixture was stirred for 15 min. The reaction mixture was concentrated in vacuo and dichloromethane (60 mL) was added, followed by a solution of 1-(diphenylmethyl)-1H-indole-2,3-dione (10.9 g, 35.0 mmol) in dichloromethane (60 mL). The reaction mixture was heated at reflux for 5 h, allowed to cool to ambient temperature and stirred for a further 16 h. Saturated aqueous ammonium chloride (30 mL) was added and the phases were separated. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration of the residue in methanol (30 mL) afforded 1-(diphenylmethyl)-3-(5-fluoro-7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-3-hydroxy-1,3-dihydro-2H-indol-2-one (10.8 g, 64%) as an off-white solid: MS (ES+) m/z 506.0 (M+23).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo and dichloromethane (60 mL)
  2. additionwas added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 5 h
  5. stirringstirred for a further 16 h
  6. customthe phases were separated
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-335c6784f758420481888d44a9e89b90
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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