Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acrylamide | HCID 6579 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine | HCID 57609300 | — |
| Catalyst | Tri-o-tolylphosphine | HCID 80271 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66839442 | HCID 66839442 | 89.5% |
Reaction Steps
Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100° C. for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935815B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-f719a0a21da949cd89edbd2cc915c80c |
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| Source note | uspto-grants-2011_05 |
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