Potassium Iodide → 2-methyl-2-{1-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propyl]-1H-indol-4-yloxy}-propionic acid ethyl ester

HRID 269954

Reaktionsgleichung

Reaktionsgleichung von HRID 269954
[CH2:1]([O:3][C:4](=[O:22])[C:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][CH2:19][CH2:20]Cl)([CH3:7])[CH3:6])[CH3:2].[CH2:23]([C:26]1[C:34]2[O:33][N:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[C:30]=2[CH:29]=[CH:28][C:27]=1[OH:39])[CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:7])([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][CH2:19][CH2:20][O:39][C:27]1[CH:28]=[CH:29][C:30]2[C:31]([C:35]([F:38])([F:37])[F:36])=[N:32][O:33][C:34]=2[C:26]=1[CH2:23][CH2:24][CH3:25])[CH3:6])[CH3:2]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 160908732-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl esterHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Produkt 1

HCID 689667202-methyl-2-{1-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propyl]-1H-indol-4-yloxy}-propionic acid ethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl ester (0.100 g, 0.31 mmol, 1.0 eq), 7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-ol (0.076 g, 0.31 mmol, 1.0 eq), potassium carbonate (0.064 g, 0.46 mmol, 1.5 eq), potassium iodide (0.010 g, 0.06 mmol, 0.2 eq), and DMF (3 mL) was heated at 110° C. for 1.5 hours. The reaction mixture was cooled to room temperature before 20 mL of water was added. The mixture was then extracted with ethyl acetate (2×20 mL). The organic layer was collected, 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/ethyl acetate (95/5) as an eluant to afford 2-methyl-2-{1-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propyl]-1H-indol-4-yloxy}-propionic acid ethyl ester (0.140 g, yield: 85%).

Aufarbeitung

  1. additionwas added
  2. extractionThe mixture was then extracted with ethyl acetate (2×20 mL)
  3. customThe organic layer was collected
  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-04828d1b35cc47e3ac413ac0bef59eb9
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449478B2

Verknüpfte Notizen

Wird geladen…