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 (D8a) (588 mg, 1.72 mmol, 1.5 equiv) in dioxan (10 ml) was added pyrrolidin-2-one (120 μl, 1.14 mmol, 1 equiv), Cs2CO3 (720 mg, 2.21 mmol, 2 equiv), Xantphos (51 mg, 0.09 mmol, 0.08 equiv) and tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.03 mmol, 0.026 equiv). The reaction mixture was stirred at 100° C. for 16 h, then cooled to room temperature and filtered through a pad of celite and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc) yielded 3,5-bis-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (B24) (411 mg, 79%) as light yellow solid. [M+H]+=303.2

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07253198B2
Source dataset	uspto-grants-2007_08
ORD ID	ord-ac2b2fd536d54a398ebd80f4f4cbf6c0
Source note	uspto-grants-2007_08