Acrylamide → HCID 59179418, compound
Reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[C:11]([NH2:15])(=[O:14])[CH:12]=[CH2:13].C([O-])(=O)C.[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(=O)([O-])O.[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2](/[CH:13]=[CH:12]/[C:11]([NH2:15])=[O:14])[C:7]=2[CH:8]=[CH:9]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 4-chlorofuro[3,2-c]pyridine (1.00 g, 6.51 mmol), acrylamide (694 mg, 9.77 mmol), sodium acetate (641 mg, 7.81 mmol), tetrabutylammonium bromide (2.31 g, 7.16 mmol), tri-o-tolylphosphine (396 mg, 1.30 mmol) and palladium(II) acetate (146 mg, 0.65 mmol) in N,N-dimethylformamide (20 mL) was stirred at 140° C. for 16 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) to give the title compound (508 mg, yield 41%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90)
Sources & evidence
- ORD record
- ord-e6e301dfc0ab477cb37cb7205530a82a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273761B2
Reaction notes
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