1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester → 1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester

HRID 1481187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481187
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[C:24]([Cu])#[N:25]>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

Komponenten

5

Edukt 2

HCID 865954711-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 898128781-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl esterAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester (0.91 g, prepared according to Arend et al. WO 2004108681) and CuCN (436 mg) in DMF (5 mL) was refluxed for 1 h; then cooled, diluted with DCM, filtered, then washed with water, dil. NaCl solution, dried over sodium sulphate, filtered, concentrated, the residue was column purified to give the desired product (195 mg). LC MS ESI: 337 (M+1)+.

Aufarbeitung

  1. temperaturewas refluxed for 1 h
  2. temperaturethen cooled
  3. filtrationfiltered
  4. washwashed with water, dil. NaCl solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-baaa232e9f2e4518a02a538bc0201b79
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409892B2

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