Tris(furan-2-yl)phosphane → HCID 59749457, compound

HRID 747251Notes

Reaction equation

HRID 747251 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1I.C[Sn](C)(C)[C:19]1[S:23][C:22]([C:24]2[CH2:28][CH:27]([CH2:29][OH:30])[O:26][N:25]=2)=[CH:21][CH:20]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1[C:19]1[S:23][C:22]([C:24]2[CH2:28][CH:27]([CH2:29][OH:30])[O:26][N:25]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 20788885Compound 3HCID 59749480{3-[5-(Trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanol

Product 1

HCID 59749457HCID 59749457, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)Catalyst

Conditions

Temperature
90 °C

Procedure

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one (195 mg, 0.58 mM), {3-[5-(trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanol (200 mg, 0.58 mM), tris(dibenzylideneacetone) dipalladium (0)-chloroform adduct (60 mg, 0.058 mM) and tri-2-furylphosphine (27 mg, 0.116 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 (60 mg).

Workup

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (5 ml) was added
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-9d6052729fdb4a499355a88414d244fa
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…