Tetrahydrofuran → (5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 456798Notes

Reaction equation

HRID 456798 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]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1I.O1CCCC1.C(N(CC)CC)C.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35]>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.[Pd].[Pd].[Cu](I)I.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11257720(R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one2×

Product 1

HCID 58625197(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneYield 257.5%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 6, 0.50 g, 1.3 mmol), tris(dibenzylideneacetone)dipalladium (0) (24 mg, 0.026 mmol), tri-2-furylphosphine (12 mg, 0.05 mmol), and copper iodide (5.0 mg, 0.013 mmol) were combined in a flask and degassed. Tetrahydrofuran (7.5 ml), triethylamine (0.54 g, 5.4 mmol) and a minimal amount of 1-methyl-2-pyrrolidinone (1.5 ml) were added to obtain a brown solution. (Trimethylsilyl)acetylene (0.18 g, 1.8 mmol) was added and the reaction was stirred at room temperature overnight. The solution was adsorbed onto silica gel and chromatographed eluting with ethyl acetate to give the title compound as a brown oil (1.2 g) (contains 1-methyl-2-pyrrolidinone).

Workup

  1. customdegassed
  2. customto obtain a brown solution
  3. customchromatographed
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-3f74f3f6f748436091cad23e61fd58ed
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

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