Water → HCID 86694712, Verbindung

HRID 475164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475164
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[H-].[Na+].I[CH3:15].O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:15].[Br:1][C:2]1[C:3]2[C:7]([CH:8]=[C:9]([F:11])[CH:10]=1)=[N:6][N:5]([CH3:15])[CH:4]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 247287454-Bromo-6-fluoro-1H-indazole

Produkt 2

HCID 712720841425932-77-9Ausbeute 12 %HCID 86694712HCID 86694712, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-6-fluoro-1H-indazole (2.3 g, 10.7 mmol) in anhydrous DMF (36 mL) was added sodium hydride (60% dispersion in mineral oil, 0.51 g, 12.8 mmol, 1.2 eq.). After stirring at RT for 5 min, iodomethane (2.2 mL) was added, and the resulting mixture was stirred at RT overnight. The reaction mixture was poured into water (200 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with water (200 mL) and brine (50 mL), dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by SiO2 chromatography eluting with hexane:EtOAc (3:1) to afford 4-bromo-6-fluoro-1-methyl-1H-indazole as a tan solid (1.42 g, 58%) and 4-bromo-6-fluoro-2-methyl-2H-indazole (0.29 g, 12%) as a tan solid. MS (ESI): m/z=229.1 [M+1]+.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at RT overnight
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined extracts were washed with water (200 mL) and brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with hexane:EtOAc (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-79efe1a1b6df4d8b810747b5840bb029
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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