N,N-Dimethylpropargylamine → HCID 21959479, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylpropargylamine	HCID 81643	—
Reactant	3-Bromo-5-(trifluoromethyl)aniline	HCID 2735880	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Product	HCID 21959479	HCID 21959479	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 3-bromo-5-trifluoromethylaniline (1.4 g, 5.9 mmol), 1-dimethylamino-2-propyne (1.3 mL, 0.76 mmol), PdCl2(PPh3)2 (0.26 g, 0.29 mmol) and CuI (114 mg, 0.60 mmol) in 10 mL of TEA was heated at 100° C. in a sealed tube for 3 h. The resulting mixture was filtered over Celite®. The filtrate was concentrated, and the residue was purified by prep-HPLC (reverse phase) to give the aniline. MS (ES+): 243 (M+H)+; (ES−): 241 (M−H)−. Calc'd C12H13F3N2—242.24.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08247430B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-1a5030451ced486c8fbca6738b77e504
Source note	uspto-grants-2012_08