Triethylamine → 5-(3-Benzyloxy-7-cyclopent-1-enyl-naphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 643887Notes

Reaction equation

HRID 643887 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1[CH2:32][CH2:31][CH2:30][CH:29]=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([C:28]1[CH2:32][CH2:31][CH2:30][CH:29]=1)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8882CyclopenteneHCID 667506335-(3-(Benzyloxy)-7-bromonaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 667505565-(3-Benzyloxy-7-cyclopent-1-enyl-naphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-oneYield 13%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a microwave vial is added 5-(3-benzyloxy-7-bromonaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.100 g, 0.224 mmol), cyclopentene (0.04 mL, 0.453 mmol), palladium acetate (0.010 g, 0.0445 mmol), triethylamine (0.063 mL, 0.448 mmol) and acetonitrile (2 mL). The vial is capped and placed in the microwave for 15 min at 110° C. The reaction mixture is filtered over Celite and washed with acetonitrile. The filtrate is concentrated and the residue is purified via Biotage Sp1, eluting with 15-60% EtOH/H2O to afford 5-(3-benzyloxy-7-cyclopent-1-enyl-naphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.0127 g): (M−H)−=433.

Workup

  1. customThe vial is capped
  2. filtrationThe reaction mixture is filtered over Celite
  3. washwashed with acetonitrile
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified via Biotage Sp1
  6. washeluting with 15-60% EtOH/H2O

Sources & evidence

ORD record
ord-54e665997e28491db0beac0b4b96ce5a
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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