Ethyl 4-iodobenzoate → Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-quinolinyl)ethynyl]benzoate

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 4-iodobenzoate	HCID 142891	—
Reactant	7-Ethynyl-4,4-dimethyl-1-(propan-2-yl)-3,4-dihydroquinolin-2(1H)-one	HCID 19963720	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Diethylamine	HCID 8021	—
Product	Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-quinolinyl)ethynyl]benzoate	HCID 19963709	—

Reaction Steps

To a solution of 0.282 g (1.17 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-ethynyl quinoline (Compound 30) and 0.52 g (1.9 mmol) of ethyl 4-iodobenzoate in 2.5 ml of diethylamine which was degassed under argon for 30 min, was added 0.049 g (0.26 mmol) of copper(I) iodide and then 0.159 g (0.23 mmol) of bis(triphenylphosphine)palladium(II) chloride. The reaction was stirred at room temperature for 4 h. The reaction mixture was then concentrated in vacuo. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05616712
Source dataset	uspto-grants-1997_04
ORD ID	ord-f670bde99aa84cfc9e4ceb313be1e03c
Source note	uspto-grants-1997_04