Sodium Iodide → HCID 68842500, compound

HRID 660792Notes

Reaction equation

HRID 660792 reaction equation
[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

Participants

9

Reactant 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

Product 1

HCID 68842500HCID 68842500, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-63ae44b1d8204713b53b35dce27ae0c9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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