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 | 5-Bromo-2-fluoropyridine | HCID 2783168 | — |
| Reactant | HCID 66661844 | HCID 66661844 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66661906 | HCID 66661906 | — |
Reaction Steps
To a solution of (1R)-1′-({1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (130 mg, 0.00029 mol) in 1,4-dioxane (1 mL, 0.01 mol) were added 5-bromo-2-fluoropyridine (0.060 mL, 0.00058 mol), tris(dibenzylideneacetone)dipalladium(0) (1 mg, 0.000001 mol), tri-tert-butylphosphine (0.71 mg, 0.0000035 mol) and potassium fluoride (56 mg, 0.00096 mol). The mixture was heated at 110° C. under nitrogen for 30 minutes. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried and concentrated. The product was purified by CombiFlash using CH2Cl2/EtOAc (max. EA 30%). LC-MS: 429.2 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08058288B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-84e6d0556f4741b7be08a394390b4216 |
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| Source note | uspto-grants-2011_11 |
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