Iodine → HCID 178451733, Verbindung

HRID 68748

Reaktionsgleichung

Reaktionsgleichung von HRID 68748
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23]I.[OH-].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([I:23])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 674494164-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 178451733HCID 178451733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (9.70 g, 3.24 mmol) in DMF (32 mL) at room temperature was treated with iodine (1.23 g, 4.86 mmol) and KOH (grounded, 454 mg, 8.1 mmol). The resulting mixture was stirred at room temperature for 40 min, then treated with saturated Na2S2O3 aqueous solution. The resulting mixture was then extracted with EtOAc (3×). The combined extracts were washed with brine and dried over Na2SO4. The resulting mixture was filtered and concentration under reduced pressure. The resulting residue was purified by flash chromatography on silica-gel (gradient eluant 10% to 40% EtOAc in heptane) to yield the title compound as white solid.

Aufarbeitung

  1. extractionThe resulting mixture was then extracted with EtOAc (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe resulting mixture was filtered
  5. concentrationconcentration under reduced pressure
  6. customThe resulting residue was purified by flash chromatography on silica-gel (gradient eluant 10% to 40% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-98c16b4a4f534f93ada601a2380dd571
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822447B2

Verknüpfte Notizen

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