1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Bromoisoquinoline-1-carbonitrile

HRID 751064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751064
C1CCN2[C:4](=[N:5]CCC2)CC1.[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[N+:15]([O-])[CH:14]=1.C([Si](C)(C)C)#N>C1COCC1>[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:4]#[N:5])=[N:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanideHCID 8173234-Bromoisoquinoline N-oxide

Produkt 1

HCID 218749014-Bromoisoquinoline-1-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DBU (1.67 mL, 11.2 mmol) was added to a mixture of compound 13A (1.12 g, 5.00 mmol) and cyanotrimethylsilane (0.75 mL, 5.5 mmol) in THF (35 mL). The resulting homogeneous mixture was refluxed for 20 min. After concentrating under reduced pressure, the residue was purified by flash chromatography on a 5×15 cm silica gel column, eluting with 3:1 hexane:EtOAc to give compound 13B (0.95 g, 82%) as a white powder. 1H NMR (400 MHz, CDCl3) □ 8.85 (s, 1H), 8.36 (d, 1H, J=8.5 Hz), 8.28 (d, 1H, J=8.5 Hz), 7.96 (t, 1H, J=8.5 Hz), 7.89 (t, 1H, J=8.5 Hz).

Aufarbeitung

  1. temperatureThe resulting homogeneous mixture was refluxed for 20 min
  2. concentrationAfter concentrating under reduced pressure
  3. customthe residue was purified by flash chromatography on a 5×15 cm silica gel column
  4. washeluting with 3:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-dac8ed0458644873a53bf0c4acf600e0
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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