반응 #834430

반응 방정식

N-{[(5S)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

{3-[5-(trimethylstannyl)thien-2-yl]-4,5-dihydroisoxazol-5-yl}methanol

tri-2-furylphosphine

→

title compound

수율 57.5%

N-{[(5S)-3-(3-Fluoro-4-{5-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

수율 57.5%

반응 조건

후처리

1. 1
   기타The solids were degassed
2. 2
   workup.ADDITIONAnhydrous dioxane (5 ml) was added
3. 3
   온도The reaction mixture was cooled
4. 4
   기타the solvent was evaporated
5. 5
   기타The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

실험 절차

N-{[(5S)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (273 mg, 0.72 mM), {3-[5-(trimethylstannyl)thien-2-yl]-4,5-dihydroisoxazol-5-yl}methanol (250 mg, 0.72 mM), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (75 mg, 0.072 mM) and tri-2-furylphosphine (34 mg, 0.145 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (5 ml) was added and the suspension was heated at 90° C. for 16 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title compound (180 mg).

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