Sodium Iodide → HCID 68842500, Verbindung

HRID 660792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660792
[Na+].[I-].[C:3]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br)#[N:4].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:35]([O:42][C:43]1[CH:48]=[C:47](I)[CH:46]=[CH:45][C:44]=1[N:50]1[S:54](=[O:56])(=[O:55])[N:53]([CH2:57][CH2:58][Si:59]([CH3:62])([CH3:61])[CH3:60])[C:52](=[O:63])[CH2:51]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C.CCOC(C)=O.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:35]([O:42][C:43]1[CH:48]=[C:47]([CH:46]=[CH:45][C:44]=1[N:50]1[CH2:51][C:52](=[O:63])[N:53]([CH2:57][CH2:58][Si:59]([CH3:60])([CH3:61])[CH3:62])[S:54]1(=[O:55])=[O:56])[CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[C:3]#[N:4])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

9

Edukt 4

HCID 5238Sodium IodideHCID 80271Tri-o-tolylphosphineHCID 895992-(Bromomethyl)benzonitrileHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Produkt 1

HCID 68842500HCID 68842500, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Zinc dust (240 mg, 3.69 mmol) is placed in a flask and heated under vacuum to remove traces of water. DMF (10 mL) is then added under nitrogen atmosphere. Dibromoethane (0.03 mL) is added and the mixture heated until effervescence occurs. The mixture is allowed to cool to RT and chlorotrimethylsilane (0.03 mL) is added. After 30 min, NaI (165 mg, 1.1 mmol) is added followed by 2-cyanobenzyl bromide (216 mg, 1.1 mmol) and the mixture is stirred at RT for 30 min. To this mixture is added tri-o-tolylphosphine (33.5 mg) and Pd2(dba)3 (20.2 mg) followed by the dropwise addition of a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (400 mg, 0.74 mmol) in DMF (10 mL). The reaction mixture is stirred at RT for 18 h and then diluted with EtOAc and filtered through Celite. The filtrate is washed with 0.1N HCl and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-10% EtOAc/hexane as eluent to give the title compound.

Aufarbeitung

  1. temperatureheated under vacuum
  2. customto remove traces of water
  3. additionDMF (10 mL) is then added under nitrogen atmosphere
  4. additionDibromoethane (0.03 mL) is added
  5. temperaturethe mixture heated until effervescence
  6. additionchlorotrimethylsilane (0.03 mL) is added
  7. stirringThe reaction mixture is stirred at RT for 18 h
  8. filtrationfiltered through Celite
  9. washThe filtrate is washed with 0.1N HCl and brine
  10. dry with materialthen is dried over sodium sulfate
  11. customThe solvent is removed under reduced pressure
  12. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63ae44b1d8204713b53b35dce27ae0c9
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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