StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trifluoroacetic acid → 2-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

HRID 561629
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561629
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])(O)[CH3:20])=[CH:15][CH:14]=1.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=1)[NH:33][CH:32]=[CH:31]2>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])([C:31]2[C:30]3[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=[C:28]([F:27])[CH:29]=3)[NH:33][CH:32]=2)[CH3:20])=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583923532-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

Produkt 1

HCID 583923982-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

367 mg (1.66 mmol) of indium(III) chloride and 0.12 ml (1.58 mmol) of trifluoroacetic acid were added to 350 mg (1.58 mmol) of the compound from Example 75A and 308 mg (1.58 mmol) of the compound from Example 11A in 9 ml of dichloromethane at RT, and the mixture was heated under reflux for 15 min. It was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 32.5 mg (5% of theory) of the title compound as mixture of diastereomers.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 min
  3. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue 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-891e9740aaff47efafd63ad8357f1b45
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion