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5-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione → Ethyl 3-(4-chloro-2-fluorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561396
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH:9]2C(=O)O[C:12](C)([CH3:16])[O:11][C:10]2=[O:18])=[C:4]([F:31])[CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:9][C:10]([O:11][CH2:12][CH3:16])=[O:18])=[C:4]([F:31])[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 583924735-[(4-Chloro-2-fluorophenyl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Produkt 1

HCID 58392210Ethyl 3-(4-chloro-2-fluorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 702EthanolLösungsmittelHCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

5.0 mg (0.08 mmol) of copper powder were added to 3.60 g (7.79 mmol) of the compound from Example 15A in 56 ml of pyridine and 14 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the residue was taken up in ethyl acetate, washed with 1N hydrochloric acid, dried over magnesium sulfate, filtered through silica gel and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 2.23 g (70% of theory) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. washwashed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through silica gel
  7. concentrationconcentrated
  8. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-e3826bbd62f94ade872cf169e19c37d7
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

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