Cesium carbonate → (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Cyclopentyl methyl ether	HCID 138539	—
Reactant	4-Bromo-1-iodo-2-methoxybenzene	HCID 46835731	—
Reactant	(E)-Ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate	HCID 117740420	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Product	(E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate	HCID 117746872	91.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A RBF charged with xantphos (9.97 g, 17.23 mmol), pd2(dba)3 (5.26 g, 5.74 mmol), 4-bromo-1-iodo-2-methoxybenzene (74.9 g, 239 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (60.000 g, 191 mmol), cesium carbonate (100 g, 306 mmol), and 400 ml cylopentyl-methylether was heated to 90° C. overnight. The reaction mixture was then poured into water and extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was triturated with IPA leaving a yellow solid that was collected and dried yielding (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxyphenyl)amino)phenyl)acrylate (86.95 g, 174 mmol, 91% yield). m/z (ESI) 500.1 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09212182B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-29f1a2417e724eb0a2e2c81ac6aeb0c6
Source note	uspto-grants-2015_12