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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 14416Generated: October 25, 2026

Water → 3-(Phenylethynyl)-5-(trifluoromethyl)pyridin-2-amine

https://huagongshe.com/reaction/14416

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPhenylacetyleneHCID 10821—
Reactant3-Bromo-5-(trifluoromethyl)pyridin-2-amineHCID 13064155—
CatalystCopper bromide (CuBr2)HCID 24611—
CatalystHCID 178418476HCID 178418476—
SolventTriethylamineHCID 8471—
Product3-(Phenylethynyl)-5-(trifluoromethyl)pyridin-2-amineHCID 23122794—

Reaction Conditions

Temperature60 °C

Reaction Steps

Under an atmosphere of argon, to a solution of 3-bromo-5-(trifluoromethyl)pyridin-2-amine (the compound described in Bio. Org. Med. Chem., 9, 1715 (1999)) (163 mg) in triethylamine (1.5 mL), ethynylbenzene (82 μL), bis(triphenylphosphine)palladium dichloride (43 mg) and copper bromide (14 mg) were added. The reaction mixture was stirred for overnight at 60° C. To the reaction mixture, water was added and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give the title compound (26 mg) having the following physical data.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732442B2
Source datasetuspto-grants-2010_06
ORD IDord-0dbb83c791174a899436c4d40bf3aa58
Source noteuspto-grants-2010_06