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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1529200Generated: November 4, 2026

Triethylamine → HCID 58235284, compound

https://huagongshe.com/reaction/1529200

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantTriphenylphosphineHCID 11776—
ReactantTrimethylsilylacetyleneHCID 66111—
Reactant3-Amino-5-bromopyridineHCID 817681—
CatalystHCID 178418476HCID 178418476—
SolventTetrahydrofuranHCID 8028—
SolventCyclohexaneHCID 8078—
SolventEthyl AcetateHCID 8857—
ProductHCID 58235284HCID 58235284—

Reaction Steps

The title compound is synthesized according to general procedure GP2 starting from 2.0 g (11.6 mmol) 5-bromo-3-amino-pyridine and 2.3 mL (16.2 mmol) 1-trimethylsilyl-ethyne using 66 mg (0.3 mmol) CuI, 303 mg (1.2 mmol) triphenylphosphine, 243 mg (0.3 mmol) PdCl2(PPh3)2 and 19 mL (139 mmol) triethylamine in 20 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using DCM/MeOH gradient. The product precipitated on the column and is subsequently extracted from the silica gel with pure MeOH. Yield: 2.0 g (91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09090564B2
Source datasetuspto-grants-2015_07
ORD IDord-53e79f8a68744898bdb324f2dcc5e223
Source noteuspto-grants-2015_07