Tris(furan-2-yl)phosphane → 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

Participants

Role	Name	HCID	Charge
Reactant	Tris(furan-2-yl)phosphane	HCID 521585	—
Reactant	(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide	HCID 11222662	—
Reactant	{3-[5-(Trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanol	HCID 59749480	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Product	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	HCID 59749451	57.5%

Reaction Conditions

Temperature	90 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07396847B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-f0d126e2f5d54694a98183f6a9358a4d
Source note	uspto-grants-2008_07