Potassium Iodide → 5-Iodo-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 1499474

Reaktionsgleichung

Reaktionsgleichung von HRID 1499474
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:6](F)=[N:7][CH:8]=[CH:9][C:10]=1[I:11].[NH4+:13].[OH-].C([O-])(=O)C.[NH4+].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.CN(C=O)C>[I:11][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:5]=1[CH2:4][CH2:3][CH2:2][NH:13]2

Komponenten

8

Edukt 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 236572333-(3-Chloropropyl)-2-fluoro-4-iodopyridine

Produkt 1

HCID 577562535-Iodo-1,2,3,4-tetrahydro-1,8-naphthyridineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-(3-chloropropyl)-2-fluoro-4-iodopyridine (5.0 g, 17 mmol), NH4OH (100 mL, 800 mmol), ammonium acetate (18 g, 230 mmol), potassium iodide (5.5 g, 33 mmol), potassium carbonate (12 g, 87 mmol) and DMF (26 mL) was heated at 60° C. for 8 h. The mixture allowed to cool, and diluted with EtOAc. The layers were separated and the organic layer was washed with brine, dried with MgSO4, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash® apparatus, eluting with 0 to 50% EtOAc in hexanes, to give the sub-title compound (3.0 g, 69% yield). LCMS calc. for C8H10IN2(M+H)+: m/z=261.0. Found: 261.1.

Aufarbeitung

  1. temperatureto cool
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using CombiFlash® apparatus
  7. washeluting with 0 to 50% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-78e87c30a9734fc689d5da3dea89c409
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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