Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | tert-Butyl acrylate | HCID 15458 | — |
| Reactant | HCID 18404695 | HCID 18404695 | — |
| Catalyst | Tri-o-tolylphosphine | HCID 80271 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 54055857 | HCID 54055857 | 90% |
Reaction Steps
A mixture of 4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}-iodobenzene [4.0 g, Reference Example 9(a)], palladium acetate (50 mg), tri-(o-tolyl)phosphine (125 mg) and tributylamine (1.85 g) in anhydrous dimethylformamide (10 ml) was treated with tert-butyl acrylate (1.0 g). The reaction mixture was stirred at 100° C. under an atmosphere of nitrogen for 4 hours then cooled to room temperature and then poured into a mixture of ethyl acetate (50 ml) and hydrochloric acid (50 ml, 1M). The resultant solid was filtered and washed sequentially with 50 ml portions of saturated aqueous sodium bicarbonate solution, water and diethyl ether. The residue was dried under vacuum to give the title compound (3.6 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06479519B1 |
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| Source dataset | uspto-grants-2002_11 |
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| ORD ID | ord-e906ca7f838c4126ab0d9ee0d6252093 |
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| Source note | uspto-grants-2002_11 |
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