Dichloromethane → 1-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[K].CCN([CH2:17][CH3:18])CC.[CH2:19](Cl)Cl>CC(O)C.O.CCOCC>[CH2:19]=[C:17]([C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=1)[CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A stirred solution of 1-(5-bromopyridin-3-yl)ethanone (600 mg, 3.0 mmol), potassium isopopenyltrifluoroborate (148 mg, 3.0 mmol), and Et3N (1.25 mL, 9.0 mmol) in iPrOH (20 mL) and H2O (10 mL) was degassed with argon for 10 min and then PdCl2 (dppf).CH2Cl2 (74 mg, 0.09 mmol) was added and the reaction mixture was heated to reflux for 5 h. The solution was cooled to room temperature and diluted with Ether and H2O. The layers were separated and the aqueous layer was extracted with Ether (2×50 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% EtOAc in hexanes) to provide 460 mg of 1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanone.
Workup
- customwas degassed with argon for 10 min
- temperaturethe reaction mixture was heated
- temperatureto reflux for 5 h
- customThe layers were separated
- extractionthe aqueous layer was extracted with Ether (2×50 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried with Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (30% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-0328a30d6b6c44d598c9f8922879ffcd
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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