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

HRID 868811Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[CH3:9][C:10]1([CH3:16])[CH2:14][NH:13][C:12](=[O:15])[NH:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([N:13]2[CH2:14][C:10]([CH3:16])([CH3:9])[NH:11][C:12]2=[O:15])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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+).

Workup

washwas eluted with an heptan

Sources & evidence

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

Reaction notes

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