Potassium Phosphate, Tribasic → HCID 89813682, compound

HRID 525384Notes

Reaction equation

HRID 525384 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:15][C:16]1[CH:21]=[C:20](I)[CH:19]=[CH:18][N:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[Cl:15][C:16]1[CH:21]=[C:20]([N:4]2[C@@H:3]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]([CH3:14])([CH3:1])[O:6][C:5]2=[O:7])[CH:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 15165112-Chloro-4-iodopyridineHCID 2733820(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinone

Product 1

HCID 89813682HCID 89813682, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial were added (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (1 g, 5.23 mmol), 2-chloro-4-iodopyridine (1.878 g, 7.84 mmol) (commercially available from Frontier Scientific, Inc., Logan Utah), and dioxane (10.46 mL). Tribasic potassium phosphate (5.55 g, 26.1 mmol) and copper (I) iodide (0.996 g, 5.23 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) were then added to the vial. The vessel was purged with argon and then N,N′-dimethylethylenediamine (1.126 mL, 10.46 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) was added. The vessel was then irradiated at 140° C. for 40 minutes, and LC-MS indicated complete conversion to the desired product. After cooling to room temperature, the reaction mixture was passed through a syringe filtered, and the material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 10% MeOH in DCM, to provide (S)-3-(2-chloropyridin-4-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one. m/z (ESI) 303.3 (M+H)+.

Workup

  1. addition) were then added to the vial
  2. customThe vessel was purged with argon
  3. addition) was added
  4. customThe vessel was then irradiated at 140° C. for 40 minutes
  5. customthe reaction mixture was passed through a syringe
  6. filtrationfiltered
  7. customthe material thus obtained
  8. customwas absorbed onto a plug of silica gel
  9. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  10. washeluting with a gradient of 0% to 10% MeOH in DCM

Sources & evidence

ORD record
ord-251c2d9c4dfd40b4a6114ba39099abff
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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