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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1187724Generated: October 26, 2026

2,6-Dichloropyridine → (S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]pyridine-2-amine

https://huagongshe.com/reaction/1187724

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,6-DichloropyridineHCID 16989—
Reactant2-(Di-tert-butylphosphino)biphenylHCID 2734215—
Reactant(S)-1-(4-Fluorophenyl)-ethylamineHCID 2779063—
ReactantSodium t-butoxideHCID 23676156—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product(S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]pyridine-2-amineHCID 8662061941.3%

Reaction Conditions

Temperature85 °C

Reaction Steps

300 mg of 2,6-dichloropyridine, 296 mg of (S)-(−)-1-(4-fluorophenyl)ethylamine, 119 mg of 2-(di-t-butylphosphino)biphenyl, 487 mg of sodium t-butoxide and 45 mg of palladium acetate were added in turn to 6 ml of degassed toluene, and the mixture was stirred at 85° C. for 2 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 210 mg of the objective compound as pale yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08673891B2
Source datasetuspto-grants-2014_03
ORD IDord-c0d9ff73daaf48ca90f374178d85ac75
Source noteuspto-grants-2014_03