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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 335890Generated: October 30, 2026

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

https://huagongshe.com/reaction/335890

Reaction equation

Participants

RoleNameHCIDCharge
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—
SolventDimethylformamideHCID 6228—
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

Sodium carbonate (saturated, 2 mL), Pd(PPh3)4 (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-fluoropyridine-3-boronic acid (310 mg, 2.18 mmol) were combined in DMF (5 mL). The solution was heated at 85° C. overnight before being cooled to rt. The solution was diluted with water (25 ml) and filtered. The solids were triturated with MeOH 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. MS m/z=382.0 [M+H].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08883782B2
Source datasetuspto-grants-2014_11
ORD IDord-11dbbcf8b9df4defb13b9cd612c708c5
Source noteuspto-grants-2014_11