Potassium Iodide → 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole

HRID 269956

Reaktionsgleichung

Reaktionsgleichung von HRID 269956
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH2:15]([C:18]1[C:26]2[O:25][N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:22]=2[CH:21]=[CH:20][C:19]=1[OH:31])[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(OCC)(=O)C.O.CN(C=O)C>[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][O:31][C:19]3[CH:20]=[CH:21][C:22]4[C:23]([C:27]([F:30])([F:29])[F:28])=[N:24][O:25][C:26]=4[C:18]=3[CH2:15][CH2:16][CH3:17])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Produkt 1

HCID 115245536-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

4-(3-Chloropropoxy)-1H-indole (0.100 g, 0.48 mmol), 7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-ol (0.117 g, 0.48 mmol), potassium carbonate (0.099 g, 0.72 mmol), potassium iodide (0.016 g, 0.10 mmol), and DMF (5 mL) were mixed and heated at 110° C. for 1.5 hours. The mixture was cooled to room temperature. Water (10 mL) and ethyl acetate (10 mL) were added and the resultant mixture was stirred for five minutes. The organic layer was separated and aqueous layer was extracted again with ethyl acetate (10 mL). The organic layer was combined, washed with water (6×20 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo to give an oily residue, which was purified by filtering through a short silica column using hexane/dichloromethane (50/50) as an eluant to afford 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole (0.156 g, yield: 78%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted again with ethyl acetate (10 mL)
  4. washwashed with water (6×20 mL) and brine (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo
  7. customto give an oily residue, which
  8. customwas purified
  9. filtrationby filtering through a short silica column

Quellen und Nachweise

ORD-Eintrag
ord-0b0ef256a0644ea5beb904af44b7387e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449478B2

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