Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloropyridine-5-boronic acid | HCID 3845034 | — |
| Reactant | 5-Bromo-1-methylpyridin-2(1H)-one | HCID 13024027 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 59233201 | HCID 59233201 | 73% |
Reaction Steps
A mixture of 5-bromo-1-methylpyridin-2(1 H)-one (2.2 g, 11.7 mmol), 6-chloropyridin-3-ylboronic acid (1.57 g, 9.98 mmol), Na2CO3 (2.2 g, 20.76 mmol), and tetrakis(triphenylphosphine)palladium (0) (500 mg, 0.05 mmol) in dioxane:water (15:1, 20 ml) was degassed and heated at 110° C. in a microwave for 1 hr. The reaction was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. The resulting residue was purified by silica gel chromatography (AcOEt-Hexanes) to provide title compound, 5-(6-Chloropyridin-3-yl)-1-methylpyridin-2(1 H)-one (1.6 g, 73% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178534B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-105e18884c79466485816744fe341dfc |
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| Source note | uspto-grants-2012_05 |
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