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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1610085Generated: October 26, 2026

Ethyl Acetate → 3-(3-fluorophenyl)-6-nitro-1H-indazole

https://huagongshe.com/reaction/1610085

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantTributyl(3-fluorophenyl)stannaneHCID 14915092—
Reactant3-bromo-6-nitro-1H-indazoleHCID 178526431—
CatalystHCID 178418397HCID 178418397—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product3-(3-fluorophenyl)-6-nitro-1H-indazoleHCID 2226089528.4%

Reaction Conditions

Temperature180 °C

Reaction Steps

To a solution of 1.0 g of 3-bromo-6-nitro-1H-indazole in 10 ml N-methylpyrrolidone were added 2.0 g of (3-fluorophenyl)tri-n-butyltin, and 480 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 180° C. for 2 hours. To the reaction mixture was added 60 ml of ethyl acetate. The mixture was sequentially washed with water (×2) and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=1:49), to give 302 mg of the title compound as orange crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06982274B2
Source datasetuspto-grants-2006_01
ORD IDord-5fc8acd277034ec397e1110af6eb2c62
Source noteuspto-grants-2006_01