Ethyl Acrylate → ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[C:41]([O:45][CH2:46][CH3:47])(=[O:44])[CH:42]=[CH2:43]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[N:3]=[CH:4][C:5](/[CH:43]=[CH:42]/[C:41]([O:45][CH2:46][CH3:47])=[O:44])=[CH:6][C:7]=1[CH3:8]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2-bromo-5-iodo-3-methylpyridine (1.5 g) in DMF (15 mL) was added palladium(II) acetate (56.5 mg) and tri-o-tolylphosphine (230 mg) and diisopropylethylamine (3.5 mL), and ethyl acrylate (1.09 mL). The mixture was heated at 90° C. for 1 hour. Resulting mixture was poured into water and extracted with AcOEt. The organic layer was washed with water and brine, and dried over Na2SO4, and the solvent was removed in vacuo. Residual brown oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:4-1:2) to give ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate (1.00 g) as pale yellow powder.
Workup
- customResulting mixture
- extractionextracted with AcOEt
- washThe organic layer was washed with water and brine
- dry with materialdried over Na2SO4
- customthe solvent was removed in vacuo
- customwas purified by silica gel column chromatography
- washeluted with AcOEt and hexane (1:4-1:2)
Sources & evidence
- ORD record
- ord-54c05bd056724ac0873fed4f3dfcdf64
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465731B2
Reaction notes
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