Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetamide | HCID 178 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 90417857 | HCID 90417857 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90418656 | HCID 90418656 | 36% |
Reaction Steps
A solution of Example C4 in dioxane (3 mL) was treated with acetamide (0.06 g, 1.0 mmol), Cs2CO3 (0.11 g, 0.34 mmol), X-Phos (0.03 g, 0.077 mmol) and Pd2(dba)3 (0.03 g, 0.034 mmol) and heated at 80° C. overnight. The mixture was diluted with EtOAc, the solids removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/DCM) to afford N-(4-((6-(2-(isopropylamino)-4-methoxypyrimidin-5-yl)-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (60 mg, 36%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181223B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-ee60c93b04084394bf862a92c390b444 |
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| Source note | uspto-grants-2015_11 |
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