Tri-o-tolylphosphine → 5-[2-Benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660774Notes

Reaction equation

HRID 660774 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4]I.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:30]([O:37][C:38]1[CH:43]=[C:42](I)[CH:41]=[CH:40][C:39]=1[N:45]1[S:49](=[O:51])(=[O:50])[N:48]([CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[C:47](=[O:58])[CH2:46]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.[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]>[CH2:30]([O:37][C:38]1[CH:43]=[C:42]([CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])[CH:41]=[CH:40][C:39]=1[N:45]1[S:49](=[O:50])(=[O:51])[N:48]([CH2:52][CH2:53][Si:54]([CH3:56])([CH3:55])[CH3:57])[C:47](=[O:58])[CH2:46]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 689980165-[2-Benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,1,1-trifluoro-3-iodopropane (0.088 mL, 0.75 mmol) in DMF (2 mL) is added Rieke zinc (0.9 mmol) and the mixture is stirred at RT for 5 h then P(o-tolyl)3 (22.8 mg, 15 mol %), Pd2(dba)3 (13.7 mg, 3 mol %) and 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (272 mg, 0.5 mmol) is added and the mixture is stirred at RT for 18 h. The mixture is partitioned between EtOAc and 1N HCl and the organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography using a gradient of 0-15% EtOAc/hexane as eluent to give the title compound.

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. customThe mixture is partitioned between EtOAc and 1N HCl
  3. washthe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-54535a9b6f27415aac78f9b1e3e05978
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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