Triethylamine → 5-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-2-tert-butyl-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724604Notes

Reaction equation

HRID 724604 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:5]=[CH:6][C:7]=1I.[C:25]([N:29]1[C:33](=[O:34])[CH:32]=[CH:31][S:30]1(=[O:36])=[O:35])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C>CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11](=[O:12])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:31]1[S:30](=[O:35])(=[O:36])[N:29]([C:25]([CH3:27])([CH3:26])[CH3:28])[C:33](=[O:34])[CH:32]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 111168162-Tert-butyl-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trioneHCID 218787833-(3-Bromo-4-iodo-phenyl)-1,2-diphenyl-propan-1-one

Product 1

HCID 587465655-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-2-tert-butyl-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-oneYield 43%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1.36-A (25.0 mg, 51 μmol), 2-tert-butylisothiazol-3(2H)-one 1,1-dioxide (19.3 mg, 0.102 mmol), tetra-N-butylammonium chloride (21.2 mg, 76 μmol) and palladium acetate (1.71 mg, 7.6 μmol) in N,N-dimethylformamide (0.48 mL) was treated with triethylamine (0.0213 mL, 0.153 mmol). The reaction mixture was degassed by bubbling with a nitrogen balloon for 10 minutes and heated at 70° C. for 1 h. The reaction mixture was diluted with ethyl acetate (5 mL) and washed with water (5 mL) and 1 N HCl (5 mL). The organic extract was dried with magnesium sulfate, filtered, and concentrated to a crude residue which was purified by flash column chromatography to yield the desired product (12 mg, 43%). LCMS found for C28H27BrNO4S (M+H)+: m/z=552, 554.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling with a nitrogen balloon for 10 minutes
  3. additionThe reaction mixture was diluted with ethyl acetate (5 mL)
  4. washwashed with water (5 mL) and 1 N HCl (5 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue which
  9. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f631e564b7f040e69325e4976b125f86
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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