Diisopropylamine → Methyl-phenyl-carbamic Acid 4-phenylethynyl-phenyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Phenylacetylene	HCID 10821	—
Reactant	Methyl-phenyl-carbamic Acid 4-iodo-phenyl Ester	HCID 69517304	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Catalyst	HCID 178418851	HCID 178418851	—
Product	Methyl-phenyl-carbamic Acid 4-phenylethynyl-phenyl Ester	HCID 69517312	41%

Reaction Conditions

Temperature	70 °C

Reaction Steps

Phenylacetylene (1.2 mmol), diisopropylamine (1.2 mmol), CuI (0.03 mmol), Pd2(dba)3 (0.03 mmol), Pd(P(t-Bu)3)2 (0.06 mmol) and methyl-phenyl-carbamic acid 4-iodo-phenyl ester (1.0 mmol) were added to a Schlenk tube under nitrogen. The Schlenk tube was evacuated and refilled with nitrogen five times. Then dioxane (2 mL) was added and the reaction mixture was stirred at 70° C. for 8 h. The crude product was purified by flash chromatography (Quad flash 12, EtOAc-heptane) giving the title compound in 41% yield as brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07067517B2
Source dataset	uspto-grants-2006_06
ORD ID	ord-eb7c0a9a05a04a57a43010fa399d305f
Source note	uspto-grants-2006_06