Triphenylphosphine → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(3-methanesulfonamidophenylethynyl)cyclohexan-1-one

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one	HCID 15392007	—
Reactant	N-(3-iodophenyl)methanesulfonamide	HCID 21830928	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Triethylamine	HCID 8471	—
Product	3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(3-methanesulfonamidophenylethynyl)cyclohexan-1-one	HCID 21830934	58.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 1-iodo-3-methanesulfonamidobenzene (0.19 g, 0.64 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.3 h, was cooled to room temperature and was concentrated in vacuo. The residue was purified by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, to provide the title compound as a tan solid (0.18 g, 58%), m.p. 59°-62° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05891883
Source dataset	uspto-grants-1999_04
ORD ID	ord-c45e7ddba5fe4c299ff44815d0eee6f6
Source note	uspto-grants-1999_04