1-Bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester → 1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

HRID 2077210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2077210
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4].[Cu][C:26]#[N:27]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:26]#[N:27])[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 866170821-Bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 671104881-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl esterAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.02 g, 2.63 mmol), copper (I) cyanide (470 mg, 5.25 mmol) and anhydrous dimethylformamide (8.8 mL) was refluxed for ten minutes before it was cooled to room temperature quenched with water and ethyl acetate. The slurry was filtered. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (727 mg): MS: (+) m/z 334.83 (M+1).

Aufarbeitung

  1. temperaturewas refluxed for ten minutes before it
  2. customquenched with water and ethyl acetate
  3. filtrationThe slurry was filtered
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-686686b115bf4f28a322df65b68b73e3
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928120B2

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