2-Bromo-5-fluorobenzonitrile → HCID 67416726, compound

Participants

Role	Name	HCID	Charge
Reactant	2-Bromo-5-fluorobenzonitrile	HCID 93654	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 67416726	HCID 67416726	—

Reaction Conditions

Temperature	105 °C

Reaction Steps

A mixture of piperazine-1-carboxylic acid tert-butyl ester (1.05 g, 5.65 mmol), 2-bromo-5-fluoro-benzonitrile (1.13 g, 5.65 mmol), Pd2(dba)3 (259 mg, 0.283 mmol), xanthphos (490 mg, 0.848 mmol), sodium tert-butoxide (1.63 g, 16.95 mmol) in anhydrous 1,4-dioxane (10 ml) was heated at 100-110° C. in a sealed tube for 1 h. After cooled to room temperature, the mixture was filtered through celite then concentrated before purified by chromatography (hexanes/EtOAc) to provide compound as indicated (1.31 g, 76%). m/z (M+1) 306.21.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08044041B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-37deac8c810940708a3fd2fd02aaafa5
Source note	uspto-grants-2011_10