Stannane, tributyl(1-ethoxyethenyl)- → N-[5-(1-ethoxyvinyl)pyridin-3-yl]acetamide

HRID 1712918Notes

Reaction equation

HRID 1712918 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:17]([O:19][CH2:20][CH3:21])=[CH2:18])CCC>CN(C=O)C.[F-].[K+].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>[CH2:20]([O:19][C:17]([C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[N:6][CH:7]=1)=[CH2:18])[CH3:21]

Participants

6

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 18624575N-(5-bromopyridin-3-yl)acetamide

Product 1

HCID 59463096N-[5-(1-ethoxyvinyl)pyridin-3-yl]acetamide

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(5-bromopyridin-3-yl)acetamide (2.7 mmol) and Pd(PPh3)2Cl2 (0.13 mmol) in DMF (5 mL) under an atmosphere of nitrogen was added tributyl(1-ethoxyvinyl)stannane (2.97 mmol). The reaction was allowed to stir at 80° C. until for approximately 24 hrs. The reaction mixture was allowed to cool to rt and then diluted with aq KF solution (10 mL) and allowed to stir for 30 min. A thick white precipitate formed and was filtered. The filter cake was washed with water and Et2O. The filtrate was diluted with water and extracted with Et2O. The organic solutions were combined, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give N-[5-(1-ethoxyvinyl)pyridin-3-yl]acetamide in quantitative yield. LCMS: (FA) ES+ 205.2.

Workup

  1. temperatureto cool to rt
  2. stirringto stir for 30 min
  3. customA thick white precipitate formed
  4. filtrationwas filtered
  5. washThe filter cake was washed with water and Et2O
  6. additionThe filtrate was diluted with water
  7. extractionextracted with Et2O
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-552a3aa7b5d2437fbb9e4c0af359ab75
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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