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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557879Generated: October 31, 2026

1,4-Dioxane → HCID 66661906, compound

https://huagongshe.com/reaction/557879

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DioxaneHCID 31275—
ReactantTris(1,1-dimethylethyl)phosphineHCID 83681—
ReactantPotassium FluorideHCID 522689—
Reactant5-Bromo-2-fluoropyridineHCID 2783168—
ReactantHCID 66661844HCID 66661844—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventEthyl AcetateHCID 8857—
ProductHCID 66661906HCID 66661906—

Reaction Conditions

Temperature110 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058288B2
Source datasetuspto-grants-2011_11
ORD IDord-84e6d0556f4741b7be08a394390b4216
Source noteuspto-grants-2011_11