Tributylvinyltin → HCID 21702077, compound

HRID 2224367Notes

Reaction equation

HRID 2224367 reaction equation
Br[C:2]1[C:3]([NH:8][C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:12]([Sn](CCCC)(CCCC)C=C)[CH2:13]CC>C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+].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>[CH:12]([C:2]1[C:3]([NH:8][C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH2:13]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 819143N-(3-Bromopyridin-2-yl)acetamide

Product 1

HCID 21702077HCID 21702077, compoundYield 46.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred mixture of N-(3-Bromo-pyridin-2-yl)-acetamide (1.20 g, 5.58 mmol) in anhydrous toluene (40 mL) under argon was added Tri-n-butyl(vinyl)tin (3.25 mL, 11.1 mmol) and Bis(triphenylphosphine)Palladium dichloride (0.40g, 0.57 mmol). This mixture was heated at 95° C. for 30 minutes and cooled to room temperature. This mixture was then diluted with saturated NaHCO3 solution (100 mL) and extracted with EtOAc (3×120 mL). The combined EtOAc extracts were dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 35 g column, eluted with CH2Cl2-EtOAc, detected at 220 nM to give 420 mg of N-(3-Vinyl-pyridin-2-yl)-acetamide 78C in 46% yield.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×120 mL)
  3. dry with materialThe combined EtOAc extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by a ISCO auto CombiFlash with a RediSep 35 g column
  7. washeluted with CH2Cl2-EtOAc

Sources & evidence

ORD record
ord-4b85d29d7a214e118ec31137ab6d2b13
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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