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Potassium Iodide → {4-[3-(7-Propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester

HRID 269957
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 269957
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:27]=[CH:26][C:18]4[C:19]([C:22]([F:25])([F:24])[F:23])=[N:20][O:21][C:17]=4[C:16]=3[CH2:28][CH2:29][CH3:30])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:31][O:32][C:33](=[O:36])[CH2:34]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:31][O:32][C:33](=[O:36])[CH2:34][N:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:27]=[CH:26][C:18]4[C:19]([C:22]([F:24])([F:23])[F:25])=[N:20][O:21][C:17]=4[C:16]=3[CH2:28][CH2:29][CH3:30])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 115245536-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole

Produkt 1

HCID 11569417{4-[3-(7-Propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole (0.100 g, 0.24 mmol), methyl-2-bromoacetate (0.109 g, 0.72 mmol), potassium carbonate (0.050 g, 0.36 mmol), potassium iodide (0.008 g, 0.05 mmol), and acetonitrile (15 mL) was stirred and refluxed for 12 hours. The mixture was cooled to room temperature and filtered to remove suspended salts. The solvent was removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was collected, washed with water (2×20 mL) and brine (2×20 mL), and then dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatograph over silica gel using hexane/ethyl acetate (95/5) as an eluant to afford {4-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester (0.089 g, yield: 76%).

Aufarbeitung

  1. temperaturerefluxed for 12 hours
  2. filtrationfiltered
  3. customto remove
  4. customThe solvent was removed in vacuo
  5. customthe residue partitioned between dichloromethane and water
  6. customThe organic layer was collected
  7. washwashed with water (2×20 mL) and brine (2×20 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was removed
  10. customthe residue was purified by flash chromatograph over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-394f7bbd21e94f00a5e6f45824a8d3ac
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07449478B2

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