Triethylamine → HCID 68839387, compound

HRID 660503Notes

Reaction equation

HRID 660503 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.[CH2:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:31]=[CH2:32].C(N(CC)CC)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:32]=[CH:31]/[CH2:30][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9309AllylbenzeneHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68839387HCID 68839387, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °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, 0.184 mmol) in MeCN (5 mL) in a pressure vessel is added allylbenzene (22 mg, 0.184 mmol), Pd(OAc)2 (3 mg) and triethylamine (186 mg, 1.84 mmol) and the mixture is heated at 100° C. for 10 h. The solvent is evaporated and the residue is purified by flash chromatography using a gradient of 10% to 40% EtOAc/hexane as eluent to give the title compound as a yellow foam.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4ebf77c3fb4f4696ba83e9a3d2f502a5
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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