3-Methyl-5-(tributylstannyl)isoxazole → (5R)-3-(3-fluoro-4-(3-methylisoxazol-5-yl)phenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

HRID 1371822Notes

Reaction equation

HRID 1371822 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1I.C([Sn](CCCC)(CCCC)[C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1[C:27]1[O:31][N:30]=[C:29]([CH3:32])[CH:28]=1

Participants

5

Reactant 2

HCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one2×

Product 1

HCID 9950622(5R)-3-(3-fluoro-4-(3-methylisoxazol-5-yl)phenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-oneYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 2, 2.08 g, 5.20 mmol) was dissolved in anhydrous 1,4-dioxane (10 ml) and degassed and placed under argon. Bis(triphenylphospine)palladium(II) chloride (0.145 g, 0.210 mmol) was added followed by dropwise addition of 5-(tributylstannyl)-3-methylisoxazole (2.41 g, 6.50 mmol) (Sakamoto, T. et al., Tetrahedron, 47, 28, 5111–5118) in 1,4-dioxane (2 ml). The reaction was degassed and heated at 100° C. for 48 hours. The solvent was removed under vacuum and the residue was dissolved in acetonitrile and washed with hexanes. The acetonitrile layer was concentrated to give a yellow solid (1.64 g) that was adsorbed onto silica gel and purified by flash chromatography using 10–20% acetone/dichloromethane. Relevant fractions were concentrated to give an off-white solid (1.50 g).

Workup

  1. customdegassed
  2. customThe reaction was degassed
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in acetonitrile
  5. washwashed with hexanes
  6. concentrationThe acetonitrile layer was concentrated

Sources & evidence

ORD record
ord-85542233bcfb4a2d80b83e741f72de20
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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