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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557258Generated: October 30, 2026

Water → HCID 131729277, compound

https://huagongshe.com/reaction/557258

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTrimethylsilylacetyleneHCID 66111—
ReactantDiisopropylethylamineHCID 81531—
Reactant2-Amino-3-bromopyridineHCID 817700—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductHCID 131729277HCID 13172927794.3%

Reaction Conditions

Temperature70 °C

Reaction Steps

To a solution of 2-amino-3-bromopyridine (5.72 g, 33.1 mmol) in N-methylpyrrolidinone (120 mL) were added trimethylsilyl acetylene (9.36 mL, 66.2 mmol), tetrakis(triphenyl phosphine) palladium (0) (1.91 g, 1.66 mmol), copper (I) iodide (630 mg, 3.31 mmol) and N,N-diisopropyl ethyl amine (11.5 mL, 66.2 mmol) at room temperature, which was stirred at 70° C for 6 hours under a nitrogen atmosphere. To the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (5.94 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058444B2
Source datasetuspto-grants-2011_11
ORD IDord-8234492ea94a49018b62a0b502a19dff
Source noteuspto-grants-2011_11