Trimethylsilylacetylene → Dipropyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	[1-(4-Bromophenyl)-cyclopropyl]dipropylamine	HCID 22568796	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Triethylamine	HCID 8471	—
Product	Dipropyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine	HCID 22568945	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

Using General Procedure D; [1-(4-bromophenyl)-cyclopropyl]-dipropylamine (Intermediate 121, 150.0 mg, 0.50 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (10.0 mg, 0.05 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (35.0 mg, 0.05 mmol). The resulting reaction mixture was heated to 70° C. for 5 d. The title compound was isolated by chromatography (0-3% EtOAc-hexanes).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06399774B1
Source dataset	uspto-grants-2002_06
ORD ID	ord-e9bd40fc929f42b9ace4dfc391abf266
Source note	uspto-grants-2002_06