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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632887Generated: October 30, 2026

Triethylamine → HCID 58235212, compound

https://huagongshe.com/reaction/632887

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantTriphenylphosphineHCID 11776—
ReactantTrimethylsilylacetyleneHCID 66111—
Reactant3-Bromo-5-hydroxypyridineHCID 599529—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventTetrahydrofuranHCID 8028—
SolventCyclohexaneHCID 8078—
SolventEthyl AcetateHCID 8857—
ProductHCID 58235212HCID 58235212—

Reaction Steps

The title compound is synthesized according to general procedure GP2 starting from 2.0 g (11.6 mmol) 5-bromo-3-hydroxy-pyridine and 2.3 mL (16.2 mmol) 1-trimethylsilyl-ethyne to 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. Yield: 2.0 g (91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321771B2
Source datasetuspto-grants-2016_04
ORD IDord-e448bf485d01457f921f52969ffa42b4
Source noteuspto-grants-2016_04