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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916544Generated: October 26, 2026

Triethylamine → 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrile

https://huagongshe.com/reaction/1916544

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant2-Chloro-5-(4-chlorophenyl)nicotinonitrileHCID 2764042—
Reactant1-(4-But-3-ynyl-benzyl)-pyrrolidineHCID 85969843—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventDimethylformamideHCID 6228—
Product5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrileHCID 10002556—

Reaction Conditions

Temperature50 °C

Reaction Steps

Under an argon atmosphere 1.9 mg (0.1 mmol) CuI and 7 mg (0.1 mmol) Pd(PPh3)2Cl2 are added to a solution of 50 mg (0.2 mmol) 2-chloro-5-(4-chloro-phenyl)-nicotinonitrile and 43 mg (0.2 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine in 2 mL DMF and 5 mL (20 mmol) triethylamine and the reaction mixture is stirred for 18 h at 50° C. The mixture is evaporated down i. vac., the residue is taken up in water, extracted exhaustively with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is is purified by HPLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-07cd0e9a4ced487dae30e68ad4b8edc2
Source noteuspto-grants-2013_12