Potassium Carbonate → HCID 58790312, compound

HRID 418716Notes

Reaction equation

HRID 418716 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)CCN.I[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[NH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25]>[Cu]I.O1CCOCC1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])[CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 66053N,N-DimethylethylenediamineHCID 707143-Iodopyridine

Product 1

HCID 58790312HCID 58790312, compoundYield 94%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
125 °C

Procedure

In a sealed flask, a stirred mixture of CuI (37 mg, ˜0.2 mmol) and potassium carbonate (2.70 g, 19.5 mmol) was degassed for 15 min. N,N-dimethylethylenediamine (146 μL, ˜1.0 mmol), 3-iodopyridine (2.00 g, 9.8 mmol), 2-pyrrolidinone (˜1 g, 11.7 mmol) and 1,4-dioxane (10 mL) were added, respectively (A. Klapars, J. C. Antilla, X. Huang S. L. Buchwald J. Am. Chem. Soc. 2001, 123. 7727-7729). The flow of nitrogen was removed, and the reaction mixture was then heated at 125° C. for 18 h. After cooling to room temperature the reaction mixture was filtered, rinsed with ethyl acetate, and concentrated. The crude product was purified by flash column chromatography (eluents MeOH/CH2Cl2: 2/98 to 5/95) to afford title compound 349 (1.49 g, 94% yield) as a yellow oily liquid. MS (m/z): 163.1 (M+H)+.

Workup

  1. customwas degassed for 15 min
  2. customThe flow of nitrogen was removed
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. filtrationwas filtered
  5. washrinsed with ethyl acetate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (eluents MeOH/CH2Cl2: 2/98 to 5/95)

Sources & evidence

ORD record
ord-ad0615dd33104ef1810ee1745bc127c7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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