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HCID 59375395, Verbindung → HCID 59375368, Verbindung

HRID 2193030
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2193030
[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([CH3:18])=[CH2:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]>[Pd]>[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([CH:16]([CH3:18])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 59375395HCID 59375395, Verbindung

Produkt 1

HCID 59375368HCID 59375368, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine (50 mg, 0.161 mmol) and 5% Pd on Carbon; Type A470129-5® (Johnson Matthey) (5 mg, 0.161 mmol) were combined in a vial. The vial was flushed with nitrogen for several minutes, and then EtOH (1.0 ml) was added. The reaction mixture was stirred under hydrogen (balloon pressure) for 6 hr. The reaction mixture was flushed with nitrogen, diluted with EtOAc (5 mL), and then filtered through a syringe filter to remove Pd/C. The filtrate was concentrated, and the resulting residue was adsorbed on to silica gel, then purified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient to afford 1-butoxy-9-fluoro-6-isopropylbenzo[c]-1,6-naphthyridine. LRMS (ESI) calc'd for (C19H21FN2O) [M+H]+, 313.2; found 313.1.

Aufarbeitung

  1. customThe vial was flushed with nitrogen for several minutes
  2. additionEtOH (1.0 ml) was added
  3. customThe reaction mixture was flushed with nitrogen
  4. additiondiluted with EtOAc (5 mL)
  5. filtrationfiltered through a syringe
  6. filtrationfilter
  7. customto remove Pd/C
  8. concentrationThe filtrate was concentrated
  9. custompurified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-3e2b597425094865aa8760e2b3107434
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329722B2

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