Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 2-Bromo-5-methylpyridine | HCID 564216 | — |
| Reactant | (1R)-1'-{[1-(4-bromophenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one | HCID 66661876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 66661609 | HCID 66661609 | — |
Reaction Steps
To a solution of (1R)-1′-{[1-(4-bromophenyl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (20 mg, 0.00005 mol, prepared as example 238) in 1,4-dioxane (0.2 mL, 0.002 mol) were added tris(dibenzylideneacetone)dipalladium(0) (0.2 mg, 0.0000002 mol), tri-tert-butylphosphine (0.12 mg, 5.8×10−7 mol), potassium fluoride (9.3 mg, 0.00016 mol) and 2-bromo-5-methylpyridine (0.012 g, 0.000073 mol), and the mixture was heated at 110° C. for 30 minutes. The reaction mixture was filtered and the filtrate was diluted with methanol. The product was isolated and purified with prep-HPLC. LC-MS: 425.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07776874B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-7b05399d144f4b7ebf452f915ae808c6 |
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| Source note | uspto-grants-2010_08 |
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