Sodium Iodide → HCID 68842500, 화합물

HRID 660792노트

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HRID 660792 반응식
[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

참가 물질

9

반응물 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

생성물 1

HCID 68842500HCID 68842500, 화합물

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63ae44b1d8204713b53b35dce27ae0c9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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