1-(2,4-Bis-trifluoromethyl-benzyl)-3-iodo-1H-indazole-5-carbaldehyde → 1-[2,4-bis(trifluoromethyl)benzyl]-3-cyano-1H-indazol-5-carbaldehyde

HRID 2400971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2400971
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[O:16])=[CH:12][CH:13]=2)[C:8](I)=[N:7]1.[C:28]([Cu])#[N:29]>CN(C=O)C>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[O:16])=[CH:12][CH:13]=2)[C:8]([C:28]#[N:29])=[N:7]1

Komponenten

4

Edukt 2

HCID 866545851-(2,4-Bis-trifluoromethyl-benzyl)-3-iodo-1H-indazole-5-carbaldehydeHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 866597001-[2,4-bis(trifluoromethyl)benzyl]-3-cyano-1H-indazol-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 1-[2,4-bis(trifluoromethyl)benzyl]-3-iodo-1H-indazol-5-carbaldehyde (2 mmol) and CuCN (5 mmol) in DMF (5 mL) was heated under microwave irradiation at 170° C. for 30 min. The mixture was partitioned between EtOAc and water. The EtOAc extracts were combined, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes 1:4 v/v) to afford 1-[2,4-bis(trifluoromethyl)benzyl]-3-cyano-1H-indazol-5-carbaldehyde as a white solid.

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc and water
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (EtOAc/hexanes 1:4 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-c54e8649754642ed9ac119210334c214
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796256B2

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