Water → HCID 22137280, compound

HRID 1827575Notes

Reaction equation

HRID 1827575 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8].[CH2:29]([OH:32])[CH:30]=[CH2:31].C(=O)(O)[O-].[Na+].O>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][C:22]([CH2:31][CH2:30][CH:29]=[O:32])=[CH:21][CH:20]=1)[S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8]

Participants

9

Reactant 4

HCID 962WaterHCID 7858Allyl Alcohol2×HCID 516892Sodium Bicarbonate2×HCID 22137278HCID 22137278, compound

Product 1

HCID 22137280HCID 22137280, compoundYield 64.4%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalyst2×HCID 167845palladium(II) acetateCatalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(3-hydroxy-benzyl)-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide (0.36 g, 0.71 mmol) in 3 mL dimethylformamide was added allyl alcohol (0.121 mL, 1.77 mmol), Pd(OAc)2, sodium bicarbonate (0.149 g, 1.77 mmol), and tetrabutylammonium chloride (0.197 g, 0.71 mmol). The reaction mixture was stirred at 50° C. for 24 hr. Additional allyl alcohol (0.121 mL, 1.77 mmol), Pd(OAc)2, sodium bicarbonate (0.060 g, 0.71 mmol), and tetrabutylammonium chloride (0.098 g, 0.36 mmol) were added and the reaction mixture was stirred at 50° C. for an additional 24 hr. The reaction mixture was allowed to cool, water and ethyl acetate were added, and the mixture was filtered through diatomaceous earth. The filtrate was washed with water and the organic layer was dried (magnesium sulfate) and concentrated in vacuo. Medium pressure silica gel chromatography of the residue (3:1 hexanes:ethyl acetate) afforded 0.20 g (64%) of the title compound. MS 436.2 (M−1)+

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for an additional 24 hr
  2. temperatureto cool
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. washThe filtrate was washed with water
  5. dry with materialthe organic layer was dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60868386ec854a0ca73b7de38f52afe9
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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