Cesium carbonate → 1-(6-Bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	4,4-Dimethylimidazolidin-2-one	HCID 232656	—
Reactant	2-Bromo-5-iodopyridine	HCID 4738271	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Toluene	HCID 1140	—
Product	1-(6-Bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one	HCID 86680740	85.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a suspension of 2-bromo-5-iodopyridine (1.0 g, 3.52 mmol), 4,4-dimethyl-imidazolidin-2-one (CAS 24572-33-6) (400 mg, 3.52 mmol, 1.0 equiv.), cesium carbonate (1.72 g, 5.28 mmol, 1.5 equiv.), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (82 mg, 0.141 mmol, 0.04 equiv.) in 10 ml of toluene was added under argon atmosphere tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (Pd2 (dba)3*CHCl3) (73 mg, 0.07 mmol, 0.02 equiv.). The mixture was stirred for 1 hour at 100° C. The mixture was directly loaded on a 50 g silicagel column and was eluted with an heptan:ethyl acetate gradient 100:0 to 0:100 and an ethyl acetate:methanol gradient 100:0 to 80:20. The desired 1-(6-bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one (810 mg, 85% yield) was obtained as a light yellow solid, MS: m/e=207.1/272.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08969338B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-420c7584a9114c51a52d67b0c59e5d65
Source note	uspto-grants-2015_03