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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 335733Generated: October 25, 2026

Dimethylformamide → (S)-2-amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol

https://huagongshe.com/reaction/335733

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium CarbonateHCID 10340—
Reactant2-Fluoropyridine-3-boronic acidHCID 2783270—
Reactant(S)-2-amino-7'-bromo-4'-fluoro-5H-spiro[oxazole-4,9'-xanthen]-2'-olHCID 58466133—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Product(S)-2-amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-olHCID 67242768—

Reaction Conditions

Temperature85 °C

Reaction Steps

A RBF was charged with sodium carbonate (2 M, 2 mL), tetrakis(triphenylphosphine)palladium (0.237 g, 0.205 mmol), (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (0.75 g, 2.054 mmol), and 2-fluoro-3-pyridineboronic acid (0.579 g, 4.11 mmol) and DMF (5 ml). The solution was heated at 85° C. overnight. The solution was diluted with water (25 ml) and filtered. The solids were triturated with methanol and dried under vacuum to afford (S)-2-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol as a tan solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08883782B2
Source datasetuspto-grants-2014_11
ORD IDord-3e919b83f279409999925a4fb449a977
Source noteuspto-grants-2014_11