Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acrylamide | HCID 6579 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 4-Chlorofuro[3,2-c]pyridine | HCID 2779746 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 59179418 | HCID 59179418 | 41.5% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273761B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-e6e301dfc0ab477cb37cb7205530a82a |
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| Source note | uspto-grants-2012_09 |
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