Cesium carbonate → HCID 10298349, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(2-Propyn-1-yl)morpholine	HCID 412941	—
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	Diglyme	HCID 8150	—
Solvent	tert-Butyl methyl ether	HCID 15413	—
Product	HCID 10298349	HCID 10298349	40.6%

Reaction Steps

(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (1.00 g; 2.37 mmol), 4-prop-2-ynyl-morpholine (1.2 g; 9.5 mmol) PdCl2(PPh3)2 (320 mg; 0.4 mmol), Cs2CO3 (2.0 g; 6.2 mmol) and CuI (100 mg; 0.52 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, acetone/hexanes 3/7>6/4) to yield the title compound as yellow foam (445 mg; 40%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06919336B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-0cbd79874dbe40ba928a5db18c6ee96c
Source note	uspto-grants-2005_07