Sodium Iodide → HCID 70312831, Verbindung

HRID 331365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331365
[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([OH:19])[CH:5]=2.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)(=O)=O.[Na+].[I-]>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([O:19][CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)[CH:5]=2

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 703074372-Bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-oneHCID 88266393HCID 88266393, Verbindung

Produkt 1

HCID 70312831HCID 70312831, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-one (500 mg, 1.48 mmol) obtained in Step 5 of Example 82 in DMF was added K2CO3(3 eq), 3-[4-(methylsulfonyl)piperazin-1-yl]propyl methanesulfonate (669 mg, 2.23 mmol, 1.5 eq), and NaI (0.3 eq) sequentially. The mixture was heated to 60° C. for 16 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2) to obtain the title compound (66%).

Aufarbeitung

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cea1fe93e2f241bda90dff6521d838f3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877747B2

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