Cesium carbonate → HCID 10162554, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-Methyl-4-(prop-2-yn-1-yl)piperazine	HCID 13514091	—
Reactant	(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone	HCID 22349575	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Hydrochloric Acid	HCID 313	—
Solvent	Diglyme	HCID 8150	—
Solvent	tert-Butyl methyl ether	HCID 15413	—
Product	HCID 10162554	HCID 10162554	32%

Reaction Steps

(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (0.5 g; 1.18 mmol), 1-methyl-4-prop-2-ynyl-piperazine (0.33 g; 2.37 mmol), PdCl2(PPh3)2 (0.158 g; 0.22 mmol), Cs2CO3 (1.0 g; 3.1 mmol) and CuI (50 mg; 0.26 mmol) are dissolved in diethylene glycol dimethyl ether (10 ml) and N,N-diisopropylethylamine (5 ml) and heated to 140° C. for 1 hour. The reaction mixture is diluted with TBME, filtered, evaporated and purified by chromatography (SiO2, EtOAc/MeOH/NH3conc 100/0/0>90/10/1) to yield the crude title compound as brown foam. The latter is dissolved in 2N HCl, washed with EtOAc, Na2CO3 added to the aqueous phase and extracted with EtOAc. The organic phase is filtered through Alox and evaporated to give the pure product as yellow foam (177 mg; 32%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06919336B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-c4d1e256d6fb4a36ba975b88c3925956
Source note	uspto-grants-2005_07