Trifluoroacetic acid → 3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

HRID 1715216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715216
O[C:2]1([C:17]2[C:25]([OH:26])=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]1=[O:16].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(OCC)(=O)C>[OH:26][C:25]1[C:17]([CH:2]2[C:6]3[CH:7]=[N:8][CH:9]=[CH:10][C:5]=3[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]2=[O:16])=[CH:18][C:19]2[O:23][CH2:22][O:21][C:20]=2[CH:24]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 119627723-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

Produkt 1

HCID 119627763-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one (0.15 g, 0.42 mmol), triethylsilane (1.60 mL, 10.0 mmol) and trifluroacetic acid (0.74 mL, 10.0 mmol) was stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate (100 mL), washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was triturated with diethyl ether to give the title compound as a white solid (not stable, turned to red in the air): MS (ES+) m/z 341.4 (M+1).

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-29dc221c68274e768a3d6e817c4ebda9
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799798B2

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