Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 3,5-Dibromo-1-methylpyridin-2(1H)-one | HCID 3614350 | — |
| Reactant | 2-(6-Aminopyridin-3-yl)-2-methylpropanenitrile | HCID 73555061 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86684070 | HCID 86684070 | 38.4% |
Reaction Steps
A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (35 mL), 156c (483 mg, 3.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (1.6 g, 6.0 mmol), Pd2(dba)3 (274.5 mg, 0.30 mmol), XantPhos (346.8 mg, 0.60 mmol), and cesium carbonate (4.59 g, 15 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 3 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:1 ethyl acetate/petroleum ether to afford 156d (400 mg, 38%) as a yellow solid. MS-ESI: [M+H]+ 347.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08669251B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-3977889bbdbe4233b3bd074f688807f1 |
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| Source note | uspto-grants-2014_03 |
|---|
