Cesium carbonate → 4-(3-Trifluoromethyl-pyridin-2-yl)-1-[5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-piperazin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one	HCID 47174438	—
Reactant	2-Chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole	HCID 67401380	—
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-(3-Trifluoromethyl-pyridin-2-yl)-1-[5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-piperazin-2-one	HCID 86593829	—

Reaction Steps

A mixture of 2-chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole from step (a) above (716 mg, 2 mmol), 4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-2-one from step (b) above (500 mg, 2 mmol), tris(dibenzylideneacetone) dipalladium (0) chloroform adduct (207 mg, 0.2 mmol, Strem Chemicals), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (213 mg, 0.4 mmol, Aldrich) and cesium carbonate (978 mg, 3 mmol, Aldrich) in 1,4-dioxane (2 mL) was subjected to microwave irradiation at 160° C. for 1.5 h. The mixture was cooled to room temperature, filtered, and the filtrate was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as a brown oil. MS (ESI, positive ion) m/z: 560 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08026241B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-636ca19979474591b02a1469a6c23feb
Source note	uspto-grants-2011_09