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

Sodium triacetoxyborohydride → 3-(5-((Dihydro-1H-furo[3,4-c]pyrrol-5(3H,6H,6aH)-yl)methyl)pyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile

HRID 1881332
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1881332
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=3)[NH:11][C:10]=2[OH:20])=[N:7][CH:8]=1)=O.[CH2:21]1[CH:25]2[CH2:26][NH:27][CH2:28][CH:24]2[CH2:23][O:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH2:21]1[CH:25]2[CH2:26][N:27]([CH2:1][C:3]3[CH:4]=[CH:5][C:6]([C:9]4[C:17]5[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=5)[NH:11][C:10]=4[OH:20])=[N:7][CH:8]=3)[CH2:28][CH:24]2[CH2:23][O:22]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21421150Hexahydro-1H-furo[3,4-c]pyrroleHCID 1362769533-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile

Produkt 1

HCID 1359390083-(5-((Dihydro-1H-furo[3,4-c]pyrrol-5(3H,6H,6aH)-yl)methyl)pyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrileAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

164 mg of 3-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile (0.62 mmol) from example 1.3 were dissolved in DMSO at 50° C. To this solution 134 mg (1.18 mmol) of hexahydro-1H-furo[3,4-c]pyrrole were added and the resulting deep-red solution was stirred at this temperature for 90 min. Afterwards 263 mg (1.24 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred for 4 h and then cooled to RT followed by further stirring for 16 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with sat. NaHCO3 solution. The aqueous phase was re-extracted with ethyl acetate and the combined organic phases were washed with brine (5×), dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude was purified by flash chromatography (silica gel, DCM/MeOH) yielding a yellow solid. Amount 95 mg. Yield 42%.

Aufarbeitung

  1. stirringthe mixture was stirred for 4 h
  2. stirringby further stirring for 16 h
  3. washwashed with sat. NaHCO3 solution
  4. extractionThe aqueous phase was re-extracted with ethyl acetate
  5. washthe combined organic phases were washed with brine (5×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude was purified by flash chromatography (silica gel, DCM/MeOH)
  10. customyielding a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-7342789bd60a46cda2c70e98309befe7
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318793B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion