Triethylamine → 2-((E)-4-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-but-3-enyl)-isoindole-1,3-dione

HRID 660589

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]([N:34]1[C:42](=[O:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]1=[O:44])[CH2:31][CH:32]=[CH2:33].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:33]=[CH:32]/[CH2:31][CH2:30][N:34]2[C:42](=[O:43])[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35]2=[O:44])[CH:12]=[CH:11][C:10]=1[N:16]1[CH2:17][C:18](=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:20]1(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

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 tube is added 2-but-3-enylisoindole-1,3-dione (41 mg, 0.202 mmol), Pd(OAc)2 (3 mg) and triethylamine (186 mg, 1.84 mmol) then the mixture is heated at 100° C. for 10 h. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 20-40% EtOAc/hexane as eluent to give the title compound: (M+NH4)+=635.

Workup

customThe solvent is removed under reduced pressure
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-2ff1d6f34c3642f49b908cdc4db0f860
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Linked notes

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