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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 271642Generated: October 26, 2026

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

https://huagongshe.com/reaction/271642

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 numberUS07452911B2
Source datasetuspto-grants-2008_11
ORD IDord-c63003db284d4d7885ec09985e2835b6
Source noteuspto-grants-2008_11