Dimethylformamide → Isoquinoline-6-carbonitrile

HRID 924986

Reaktionsgleichung

Reaktionsgleichung von HRID 924986
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[CH3:12][N:13](C=O)C>O.[C-]#N.[C-]#N.[Zn+2].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>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 3136816-Bromoisoquinoline

Produkt 1

HCID 23130705Isoquinoline-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under N2, a mixture of 6-bromoisoquinoline (400 mg, 1.9 mmol), Zn(CN)2 (446 mg, 3.8 mmol) and Pd(PPh3)4 (40 mg) in DMF (20 mL) was stirred at 100° C. for 1 hour. Cooled the mixture to room temperature and dissolved in water. Followed standard aqueous/EtOAc workup and purified by column chromatography (PE:EtOAc=10:1).

Aufarbeitung

  1. temperatureCooled the mixture to room temperature
  2. customFollowed standard aqueous/EtOAc workup and purified by column chromatography (PE:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9ad97890a96a449c9d00df1b02c12a4f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283229B2

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