2-(Tributylstannyl)furan → HCID 21893410, compound

HRID 720574Notes

Reaction equation

HRID 720574 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)CCC>O1CCOCC1.C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 9927066N-(2-(4-Bromophenyl)propyl)propane-2-sulfonamide

Product 1

HCID 21893410HCID 21893410, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.5 g (1.6 mmol) of material from Example 27 and 0.6 g (1.7 mmol) of 2-(tributylstannyl)-furan in 5 mL of dioxane was added 0.1 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium (0). The mixture was heated to reflux for 16 hours, cooled to ambient temperature and diluted with 5 mL of ethyl ether. The mixture was washed once with 5 mL of saturated aqueous potassium fluoride, the organic layer was separated and the aqueous portion was extracted three times with 5 mL each of ethyl ether. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography (25 g of silica gel, 25% ethyl acetate/hexane) of the residue afforded a yellow oil which was recrystallized from ethyl ether/hexane to afford 0.2 g (51%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. washThe mixture was washed once with 5 mL of saturated aqueous potassium fluoride
  4. customthe organic layer was separated
  5. extractionthe aqueous portion was extracted three times with 5 mL each of ethyl ether
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customChromatography (25 g of silica gel, 25% ethyl acetate/hexane) of the residue afforded a yellow oil which
  10. customwas recrystallized from ethyl ether/hexane

Sources & evidence

ORD record
ord-3cdbf40ed94140ba99601b8d0b832e89
Source dataset
uspto-grants-2006_11
Patent number
US07135487B2

Reaction notes

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