Cesium carbonate → Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate

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	Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate	HCID 22253055	82.4%

Reaction Conditions

Temperature	40 °C

Reaction Steps

3-Bromo-5-iodobenzoic acid methyl ester (2.044 g, 5.996 mmol) in dioxane (25 ml) was treated with 2-pyrrolidinone (433 μl, 5.696 mmol), Cs2CO3 (2.93 g, 8.994 mmol), pd2(dba)3 (110 mg, 0.12 mmol) and Xantphos (208 mg, 0.36 mmol). The reaction mixture was heated to 40° C. for 3 days, then cooled to room temperature. The reaction mixture was filtered through celite and concentrated in vacuo. Column chromatography on silica gel (EtOAc) gave D9 (1.4 g) as a brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06992103B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-3973de37196f4ebcb877a26826177032
Source note	uspto-grants-2006_01