Trifluoroacetic acid → 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

HRID 1008641

Reaktionsgleichung

Reaktionsgleichung von HRID 1008641
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH:22]=O)=[CH:16][CH:15]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[CH3:1])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 72242-MethylindoleHCID 12052TriethylsilaneHCID 10104031Methyl 4-(3-oxopropyl)benzoate

Produkt 1

HCID 670554944-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-Methyl-1H-indole (0.86 g, 5.2 mmol) and 4-(3-Oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester in 88% (1.67 g) yield.

Aufarbeitung

  1. customquenched with sat. NaHCO3 solution (50 mL)
  2. washthe organic layer was washed with sat. NaHCO3 solution, water, brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography with 10-20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ecfde929e0d141ec93b970c0ae977667
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797708B2

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