Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propionamide | HCID 6578 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86703366 | HCID 86703366 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 71575877 | HCID 71575877 | 16.8% |
Reaction Steps
Using the procedure of Example 12, N-(5-chloro-4-((2-chloropyridin-4-yl)oxy)-2-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.05 g, 0.094 mmol), propionamide (10 mg, 0.14 mmol), Cs2CO3 (0.05 g, 0.14 mmol), Xantphos (6 mg, 0.010 mmol), Pd2(dba)3 (5 mg, 0.005 mmol) and dioxane (2 mL) were combined to obtain N-(5-chloro-2-fluoro-4-((2-propionamidopyridin-4-yl)oxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (9 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.16 (s, 1H), 10.46 (s, 1H), 8.46 (d, J=7.8 Hz, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.45 (m, 3H), 7.31 (t, J=8.7 Hz, 2H), 6.62 (dd, J=5.7, 2.4 Hz, 1H), 6.50 (d, J=7.9 Hz, 1H), 4.23 (q, J=7.0 Hz, 2H), 2.28 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.0 Hz, 3H), 0.95 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 569.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08921565B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-4a75260199a844b4bb2d32857dd93f22 |
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| Source note | uspto-grants-2014_12 |
|---|
