1-(Cyclopentylsulfonyl)-3-iodobenzene → (5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one (207 mg) and 1-(cyclopentylsulfonyl)-3-iodobenzene (Example 8iii.) (202 mg) in MeCN (8 ml) and triethylamine (4 ml) was deoxygenated by bubbling a nitrogen stream through for 10 min. Copper (I) iodide (10 mg) and dichlorobis(triphenylphosphine)palladium (II) (18 mg) were added and the mixture stirred at 20° for 4 h. The solvent was evaporated in vacuo and the residues purified by using a SPE silica bond elut cartridge (10 g, silica). Elution with DCM (1vol), EtOAc-cyclohexane (1:4) (3vols), (1:3) (1vol) then (1:1) (3vols) gave the title compound (243 mg). LCMS RT=3.79 min.

Provenance & Evidence