(Triethylsilyl)acetylene → 2-(2-((Triethylsilyl)ethynyl)phenyl)propanamide

Participants

Role	Name	HCID	Charge
Reactant	(Triethylsilyl)acetylene	HCID 637947	—
Reactant	Tri-tert-butylphosphine tetrafluoroborate	HCID 2734635	—
Reactant	2-(2-Iodophenyl)propanamide	HCID 86712277	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2-((Triethylsilyl)ethynyl)phenyl)propanamide	HCID 86712278	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of 2-(2-iodophenyl)propanamide I13 (12.4 g, 45.2 mmol), ethynyltriethylsilane (9.72 mL, 54.2 mmol), PdCl2(PPh3)2 (0.634 g, 0.904 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.262 g, 0.904 mmol) and CuI (0.172 g, 0.904 mmol) in DMF (46 mL) was stirred under a nitrogen atmosphere at 70° C. for 4 hours. The volatiles were removed in vacuo and the crude residue was purified by silica gel column chromatography (Combiflash Rf, 0-30% EtOAc in cyclohexane) to give the title compound I14 as an orange oil (8.9 g, 68%). LCMS-B: rt 3.845 min; m/z 288 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238644B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-fbf5c6d2131b43f1b3590cb39128545d
Source note	uspto-grants-2016_01