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

Trifluoroacetic acid → 6-[6-methoxy-2-(1-methylcyclopropyl)-1H-indol-3-ylmethyl]pyridine-2-carbonitrile

HRID 2409994
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2409994
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[NH:25]C(=O)OC(C)(C)C)[C:11]([C:13]2([CH3:16])[CH2:15][CH2:14]2)=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(#N)C.ClCCl>[CH3:24][O:23][C:20]1[CH:19]=[C:18]2[C:17]([C:10]([CH2:9][C:7]3[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=3)=[C:11]([C:13]3([CH3:16])[CH2:15][CH2:14]3)[NH:25]2)=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86703308tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-(1-methylcyclopropyl)-2-oxoethyl]-5-methoxyphenyl}carbamate

Produkt 1

HCID 867032956-[6-methoxy-2-(1-methylcyclopropyl)-1H-indol-3-ylmethyl]pyridine-2-carbonitrileAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21877088Acetonitrile methylene chlorideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-(1-methylcyclopropyl)-2-oxoethyl]-5-methoxyphenyl}carbamate (270 mg) in acetonitrile/dichloromethane (2.1 mL/2.1 mL) was added trifluoroacetic acid (2.1 mL) under ice-cooling, and the mixture was stirred at room temperature for 44.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane), and then purified by aminopropylated silica gel column chromatography to obtain the title compound (163 mg). 1H-NMR (CDCl3) δ ppm: 0.70-0.78 (2H, m), 0.81-0.89 (2H, m), 1.33 (3H, s), 3.82 (3H, s), 4.39 (2H, s), 6.70 (1H, dd, J=2.3, 8.5 Hz), 6.80-6.85 (1H, m), 7.12-7.22 (2H, m), 7.47-7.53 (1H, m), 7.59 (1H, t, J=7.8 Hz), 7.87 (1H, br s).

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)
  8. custompurified by aminopropylated silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-668c6dcd15c5433c83b7d61c8a1c46ac
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815903B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion