Acetamide → 4-(5-Acetylamino-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	Acetamide	HCID 178	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-(5-Bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester	HCID 67400639	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(5-Acetylamino-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester	HCID 67400940	—

Reaction Steps

A mixture of 4-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester from step (a) above (300 mg, 0.677 mmol), acetamide (60 mg, 1 mmol, Aldrich), tris (dibenzylideneacetone) dipalladium (0) chloroform adduct (70 mg, 0.068 mmol, Strem Chemicals), 4,5-bis (diphenylphosphino)-9,9-dimethylxanthene (78 mg, 0.135 mmol, Aldrich) and cesium carbonate (331 mg, 1.01 mmol, Aldrich) in 1,4-dioxane (4 mL) was subjected to microwave irradiation at 170° C. for 0.5 h. The mixture was cooled to room temperature and was filtered. The filtrate was purified by silica gel column chromatography (2%-100% EtOAc/hexane) to give the title compound as a light-brown solid. MS (ESI, positive ion) m/z: 423 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07582761B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-d5be3002e82e41ae90f75cef39ecbacb
Source note	uspto-grants-2009_09