N-Iodosuccinimide → 9-bromo-4-iodo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2193021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193021
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:15]([CH3:17])[CH3:16])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.C1C(=O)N([I:27])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:15]([CH3:16])[CH3:17])=[N:7][C:8]3[C:9]([I:27])=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 593756889-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

Produkt 1

HCID 593756199-bromo-4-iodo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of 9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (81 mg, 0.26 mmol) in DMF (1.5 ml) was added NIS (86 mg, 0.38 mmol), and stirred for 24 hours at room temperature. The reaction mixture was diluted with EtOAc until a solution was formed, and washed with a mixture of 10% aqueous sodium thiosulfate and 1N NaOH. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was adsorbed on to silica gel and purified by silica gel chromatography using an EtOAc/Hexanes gradient to afford 9-bromo-4-iodo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C15H12BrIN2O) [M+H]+, 442.9; found 442.8.

Aufarbeitung

  1. customwas formed
  2. washwashed with a mixture of 10% aqueous sodium thiosulfate and 1N NaOH
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7e1f61a6836f4c1cb9a14d67b30622d8
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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