Tris(furan-2-yl)phosphane → (5R)-3-(5-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}pyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747253Notes

Reaction equation

HRID 747253 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]3)[O:10][C:9]2=[O:20])=[N:6][CH:7]=1.C[Sn](C)(C)[C:23]1[S:27][C:26]([C:28]2[CH2:32][CH:31]([CH2:33][OH:34])[O:30][N:29]=2)=[CH:25][CH:24]=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]>[OH:34][CH2:33][CH:31]1[O:30][N:29]=[C:28]([C:26]2[S:27][C:23]([C:2]3[CH:3]=[CH:4][C:5]([N:8]4[CH2:12][C@H:11]([CH2:13][N:14]5[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]5)[O:10][C:9]4=[O:20])=[N:6][CH:7]=3)=[CH:24][CH:25]=2)[CH2:32]1

Participants

5

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 59749480{3-[5-(Trimethylstannyl)thien-2-yl]4,5-dihydroisoxazol-5-yl}methanolHCID 59749508(5R)-3-(5-Bromopyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Product 1

HCID 59749430(5R)-3-(5-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}pyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-oneYield 28.3%

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-(5-Bromopyrid-2-yl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-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 5 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 (72 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-33a1105af8a14aa094853c9d1db4d647
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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