Cesium carbonate → 3,5-Bis-(2-oxo-pyrrolidin-1-yl)benzoic Acid Methyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Pyrrolidone	HCID 12025	—
Reactant	Methyl 3-bromo-5-iodobenzoate	HCID 21942573	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3,5-Bis-(2-oxo-pyrrolidin-1-yl)benzoic Acid Methyl Ester	HCID 69357758	238.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 3-bromo-5-iodobenzoic acid methyl ester (588 mg, 1.72 mmol) in dioxane (10 ml) was added 2-pyrrolidinone (120 μl, 1.14 mmol), Cs2CO3 (720 mg, 2.21 mmol), xantphos (51 mg, 0.09 mmol) and pd2(dba)3 (28 mg, 0.03 mmol). The reaction mixture was stirred at 100° C. overnight, then cooled down to room temperature and filtered through celite and concentrated in vacuo. The product was purified by column chromatography (EtOAc) which yielded D7 (411 mg) as light yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06992103B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-571ffa9281904ae49e27b3047906d727
Source note	uspto-grants-2006_01