Potassium Carbonate → HCID 610345, compound

HRID 2362268Notes

Reaction equation

HRID 2362268 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[O:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][CH2:15][O:11][C:12]2=[O:16])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 739492-OxazolidinoneHCID 145742L-Proline

Product 1

HCID 610345HCID 610345, compoundYield 27%

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of 1-bromo-4-nitrobenzene (5.00 g, 25 mmol) and oxazolidin-2-one (3.23 g, 37 mmol) in dioxane (25 mL) were added L-proline (285 mg, 2.5 mmol), CuI (238 mg, 1.2 mmol) and K2CO3 (6.90 g, 50 mmol). The resultant mixture was stirred under N2 at 110° C. for 63 h and then evaporated. The residue was diluted with EA/water (40 mL/40 mL). The mixture was filtered and the resultant aqueous layer was extracted with EA (30 mL×5). The combined organic layers were washed with brine, dried over NaSO4, concentrated and purified by silica gel column chromatography (DCM to DCM:MeOH=50:1) to afford desired as a yellow solid (1.40 g, yield 27%).

Workup

  1. customevaporated
  2. additionThe residue was diluted with EA/water (40 mL/40 mL)
  3. filtrationThe mixture was filtered
  4. extractionthe resultant aqueous layer was extracted with EA (30 mL×5)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over NaSO4
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (DCM to DCM:MeOH=50:1)
  9. customto afford

Sources & evidence

ORD record
ord-c4a31d14710a42c49bf62fdb851476f4
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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