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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916178Generated: October 30, 2026

Triethylamine → HCID 58235284, compound

https://huagongshe.com/reaction/1916178

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-pyridin-3-ylamine 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 a DCM/MeOH gradient. The product precipitated on the column and was subsequently extracted from the silica gel with pure MeOH. Yield: 2.0 g (91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618111B2
Source datasetuspto-grants-2013_12
ORD IDord-fcb94a0f10f04cff8281665cab698bc0
Source noteuspto-grants-2013_12