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

HRID 2385060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2385060
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C([Mg]Cl)(C)C.[F:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[N:25]([CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24](=[O:40])[C:23]2=[O:41].ClCCl>O1CCCC1>[C:34]1([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:25]2[C:26]3[C:22](=[CH:21][CH:20]=[CH:19][C:18]=3[F:17])[C:23]([OH:41])([C:8]3[C:9]([OH:11])=[CH:10][C:5]4[O:4][CH2:3][CH2:2][O:1][C:6]=4[CH:7]=3)[C:24]2=[O:40])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
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Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 673566781-(diphenylmethyl)-7-fluoro-1H-indole-2,3-dioneHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 685991191-(diphenylmethyl)-7-fluoro-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-oneAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) suspension of 2,3-dihydro-1,4-benzodioxin-6-ol (0.47 g, 3.0 mmol) in anhydrous tetrahydrofuran (12 mL) was added isopropylmagnesium chloride (2 M solution in tetrahydrofuran, 1.7 mL, 3.3 mmol). The reaction mixture was stirred at 0° C. for 1 h, and 7-fluoro-1-(diphenylmethyl)-1H-indole-2,3-dione (1.0 g, 3.0 mmol) and anhydrous dichloromethane (10 mL) were added. The reaction mixture was allowed to stir for 19 h at ambient temperature. The reaction mixture was concentrated in vacuo and was diluted with saturated aqueous ammonium chloride (30 mL) and ethyl acetate (30 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography and eluted with a 8% to 66% gradient of ethyl acetate in hexanes to afford 1-(diphenylmethyl)-7-fluoro-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydro-2H-indol-2-one (1.22 g, 84%) as an off-white solid: MS (ES+) m/z 475.0 (M−17).

Aufarbeitung

  1. temperatureTo a cooled
  2. stirringto stir for 19 h at ambient temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionwas diluted with saturated aqueous ammonium chloride (30 mL) and ethyl acetate (30 mL)
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  7. washThe combined organic extracts were washed with brine (100 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by column chromatography
  12. washeluted with a 8% to 66% gradient of ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-215dc75419bf484f9c1a9a35059d6350
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263606B2

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