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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029146Generated: November 1, 2026

Cesium carbonate → 1-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

https://huagongshe.com/reaction/1029146

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantPhenol, 4-amino-2-fluoro-HCID 2735918—
Reactant1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-oneHCID 58168008—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product1-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-oneHCID 5816834590%

Reaction Conditions

Temperature120 °C

Reaction Steps

Compound 83 (250 mg, 1.08 mmol), 4-amino-2-fluoro-phenol (276 mg, 2.17 mmol), and cesium carbonate (1.41 g, 4.34 mmol) were suspended in DMF (5 mL), and stirred for 30 minutes at 120° C. in microwave. The reaction mixture was diluted with H2O. The resulting precipitate was filtered. The precipitate was tritturated with MeOH, filtered, washed with MeOH, and dried under vacuum to provide 182 (312 mg, 90% yield) as a solid. LC-MS (M+H=322, obsd.=322).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-2a5d788b0d094b169f97d9ee159d4f00
Source noteuspto-grants-2014_05