5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide → 5-Iodo-1H-indazole-3-carbaldehyde

HRID 218461

Reaktionsgleichung

Reaktionsgleichung von HRID 218461
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](N(OC)C)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=[O:12]

Komponenten

4

Edukt 2

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1785200355-Iodo-1H-indazole-3-carbaldehydeAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (500 mg, 1.51 mmol), from Synthetic Preparation 6, in THF (10 mL) at 0° C. was added lithium aluminum hydride (61 mg, 1.66 mmol). After 30 min, the reaction was quenched by the slow addition of EtOAc followed by 0.4N NaHSO4, and extracted. The organic layer was washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to give 5-iodo-1H-indazole-3-carboxaldehyde (240 mg, 58.2%).

Aufarbeitung

  1. customthe reaction was quenched by the slow addition of EtOAc
  2. extractionextracted
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5fc2b1c1673d47bf8439ad9dccac66dc
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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