Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Piperidone | HCID 12665 | — |
| Reactant | 2-Bromonicotinaldehyde | HCID 4714951 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 89500826 | HCID 89500826 | 50% |
Reaction Steps
2-Bromopyridine-3-carbaldehyde a4-0 (0.5 g, 2.7 mmol, 1 eq) is dissolved in dry and degassed 1,4-dioxane (15 ml). Piperidin-2-one (0.4 g, 4.03 mmol, 1.5 eq), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.31 g, 0.538 mmol, 0.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.123 g, 0.134 mmol, 0.05 eq) and cesium carbonate (1.752 g, 5.376 mmol, 2 eq) are added. The mixture is heated in a sealed tube in a microwave oven at 120° C. for 45 min. The resulting suspension is filtered over celite and the celite washed with 1,4-dioxane. The filtrate is evaporated under reduced pressure. The residue is then dispersed in ethyl acetate, sonicated, filtered and the filtrate is evaporated under reduced pressure to afford 1.1 g of crude 2-(2-oxopiperidin-1-yl)pyridine-3-carbaldehyde a4-1 which is used in the next step without any further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067930B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-391c7b28654f481cb038c4d10a4253e0 |
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| Source note | uspto-grants-2015_06 |
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