Water → HCID 21830680, compound

HRID 1600941Notes

Reaction equation

HRID 1600941 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][CH:32]([OH:35])[C:33]#[CH:34])[CH:25]=1.O>CN(C)C=O.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:34]#[C:33][CH:32]([OH:35])[CH2:31][CH2:30][C:26]3[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 21830640HCID 21830640, compoundHCID 21830641HCID 21830641, compound

Product 1

HCID 21830680HCID 21830680, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3'-Acetyl-4-trifluoromethanesulfonyloxybiphenyl (2.0 g), (±)-5-(3-pyridyl)pent-1-yn-3-ol (1.4 g), bis(triphenylphosphine)palladium(II) chloride (0.2 g) in N,N-dimethylformamide (8 ml) and triethylamine (4.5 ml) were heated at 90° C. for 2 hours with stirring under nitrogen. After cooling the reaction was poured into water and extracted with dichloromethane. The organic solution was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (3:97) to give the sub-title compound as a pale yellow gum (1.33 g).

Workup

  1. temperatureAfter cooling the reaction
  2. extractionextracted with dichloromethane
  3. washThe organic solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (3:97)

Sources & evidence

ORD record
ord-9519502fe3f4421ea2234859878c9770
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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