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Tert-Butanesulfinamide → (+/-)-tert-Butyl 4-(1-((tert-butylsulfinyl)imino)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2173954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2173954
[CH3:1][O:2][C:3]1[C:4]([C:20](=O)[C:21]([F:24])([F:23])[F:22])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6]2.[CH3:26][C:27]([S:30]([NH2:32])=[O:31])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[C:27]([S:30]([N:32]=[C:20]([C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:10]([CH3:12])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[C:21]([F:22])([F:24])[F:23])=[O:31])([CH3:29])([CH3:28])[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 3382465Tert-ButanesulfinamideHCID 86701516tert-Butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoroacetyl)-1H-indole-1-carboxylate

Produkt 1

HCID 86701517(+/-)-tert-Butyl 4-(1-((tert-butylsulfinyl)imino)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of tert-butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoroacetyl)-1H-indole-1-carboxylate (0.45 g, 1.26 mmol) and 2-methyl-2-propanesulfinamide (0.46 g, 3.78 mmol) in toluene (12.6 mL), Zr(O-t-Bu)4 (2.52 mL, 6.30 mmol) was added at room temperature, and the reaction was heated to 100° C. After 15 minutes the reaction mixture was cooled to room temperature and diluted with EtOAc and sat. aq. brine. The resulting mixture was filtered and the layers separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 461.3 (M+H).

Aufarbeitung

  1. temperatureAfter 15 minutes the reaction mixture was cooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-ff8fdda6dc494e5cb2e5304e48998e3c
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09056874B2

Notizen zur Reaktion

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