2-Mercaptobenzoic Acid → 4-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole

HRID 383461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383461
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](SC)=[C:10]2[C:20]2[C:21]([CH3:26])=[N:22][O:23][C:24]=2[CH3:25])=[CH:5][CH:4]=1.SC1C=CC=CC=1C(O)=O.FC(F)(F)C(O)=O.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]2[C:20]2[C:21]([CH3:26])=[N:22][O:23][C:24]=2[CH3:25])=[CH:7][CH:8]=1

Komponenten

5

Edukt 4

HCID 54432-Mercaptobenzoic AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 583782154-(1-(4-Methoxyphenyl)-3-(methylthio)-1H-indol-2-yl)-3,5-dimethylisoxazole

Produkt 1

HCID 583782004-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazoleAusbeute 86 %

Versuchsvorschrift

4-(1-(4-Methoxyphenyl)-3-(methylthio)-1H-indol-2-yl)-3,5-dimethylisoxazole (the intermediate product of step (c) from the synthesis of Example 21, 140 mg, 0.38 mmol) and 2-mercaptobenzoic acid (118 mg, 0.77 mmol) were added to 5 ml of trifluoroacetic acid at RT. The mixture was stirred as a slurry at RT under an atmosphere of nitrogen over night. 2M NaOH and EtAc were added and the phases were separated. The solvents were evaporated and the residue was purified by flash chromatography with heptane/EtAc 4:1 as eluent to provide 4-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole in 86% yield. ES/MS m/z: 319.1 (M+H)

Aufarbeitung

  1. customthe phases were separated
  2. customThe solvents were evaporated
  3. customthe residue was purified by flash chromatography with heptane/EtAc 4:1 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-519f5bc359864b18afbc0a04024d84b0
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367665B2

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