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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405006Generated: October 31, 2026

Triethylamine → HCID 58235284, compound

https://huagongshe.com/reaction/1405006

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 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 numberUS08916548B2
Source datasetuspto-grants-2014_12
ORD IDord-4ec2284cc10f4a0ebedca59124e99b8a
Source noteuspto-grants-2014_12