6-Bromoisoquinoline → Isoquinoline-6-carbonitrile

HRID 598820

Reaktionsgleichung

Reaktionsgleichung von HRID 598820
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.[C:12]([Cu])#[N:13]>CN1C(=O)CCC1>[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

4

Edukt 2

HCID 3136816-BromoisoquinolineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 23130705Isoquinoline-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

6-Bromoisoquinoline (0.876 g, 4.18 mmol) purchased from Gateway Chemical Technology, Inc. was mixed with CuCN (1.12 g, 12.54 mmol) in 5 mL NMP in a microwave heating tube. The tube was heated under microwave to 150° C. for 1 hour and 170° C. for one hour. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. After removing the solvent, the remaining residue was passed through a silica gel plug using 5% 2M ammonia in MeOH in DCM as the eluant. The crude product (100 mg) was used directly in the next step.

Aufarbeitung

  1. temperatureheating tube
  2. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customAfter removing the solvent

Quellen und Nachweise

ORD-Eintrag
ord-08e90cabb20848959ae7c039aa310e8a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897619B2

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