Nitrogen → 4-Isoquinolinecarbonitrile

HRID 1470479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470479
Br[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N#N.[CH3:14][N:15](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([C:14]#[N:15])=[CH:2][N:3]=1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 6409693-Bromoisoquinoline

Produkt 1

HCID 964504-IsoquinolinecarbonitrileAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred solution of 3-bromoisoquinoline (Intermediate-12) (9.2 g, 44.2 mmol) in DMF (15 mL) were added, Pd(PPh3)4 (10.2 g, 8.84 mmol) and Zn(CN)2 (10.34 g, 88.44 mmol, 2.0 eq) and the solution was degassed with N2 for 20 min. It was then heated to 120° C. overnight. After the completion (TLC), reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (10% EtOAc:Hexanes) to afford the desired compound (3.4 g, 27.4%) as pale yellow solid.

Aufarbeitung

  1. customAfter the completion (TLC), reaction mixture
  2. temperaturewas cooled to RT
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product obtained
  6. customwas purified by flash column chromatography (10% EtOAc:Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bcda7d7fa6fa4218b3098cdbb0913636
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006442B2

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