Triethylamine → 5-{4-[(E)-2-(1-Benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660654Notes

Reaction equation

HRID 660654 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1([S:36]([N:39]2[CH2:43][CH2:42][CH2:41][CH:40]2[CH:44]=[CH2:45])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(CC)CC.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:30]1([S:36]([N:39]2[CH2:43][CH2:42][CH2:41][CH:40]2/[CH:44]=[CH:45]/[C:13]2[CH:12]=[CH:11][C:10]([N:16]3[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]3)=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:14]=2)(=[O:38])=[O:37])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-oneHCID 688399341-Benzenesulfonyl-2-vinylpyrrolidine

Product 1

HCID 688422695-{4-[(E)-2-(1-Benzenesulfonylpyrrolidin-2-yl)-vinyl]-2-benzyloxyphenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (100 mg, 0.183 mmol) in acetonitrile (2 mL) is added 1-benzenesulfonyl-2-vinylpyrrolidine (43 mg, 0.183 mmol), NEt3 (0.038 mL, 0.274 mmol), Pd(OAc)2 (2 mg, 0.034 mmol), and 2-(di-t-butylphosphino)biphenyl (4 mg) and the mixture stirred at 80° C. for 48 h. The reaction is cooled to RT and partitioned between 1N HCl and EtOAc. The organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the crude material purified by column chromatography using a gradient of 10-25% EtOAc/hexane to afford the title compound.

Workup

  1. temperatureThe reaction is cooled to RT
  2. custompartitioned between 1N HCl and EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-5855614989934193b77e0cc35a59acd7
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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