Cesium carbonate → 1-(3-Fluoro-5-iodo-pyridin-2-yl)-4,4-dimethyl-imidazolidin-2-one

HRID 1966586Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([I:9])=[CH:4][N:3]=1.[CH3:10][C:11]1([CH3:17])[CH2:15][NH:14][C:13](=[O:16])[NH:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[F:8][C:7]1[C:2]([N:14]2[CH2:15][C:11]([CH3:17])([CH3:10])[NH:12][C:13]2=[O:16])=[N:3][CH:4]=[C:5]([I:9])[CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2,3-Difluoro-5-iodopyridine (300 mg, 1.24 mmol) was dissolved in 2 ml toluene. (140 mg, 1.24 mmol, 1 equiv.) 4,4-Dimethylimidazolidin-2-one (CAS 24572-33-6) and cesium carbonate (650 mg, 1.99 mmol, 1.6 equiv.) were added and the mixture was heated to 100° C. for 4 hours. The reaction mixture was loaded directly onto a silica gel column and purified by flash chromatography eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired 1-(3-fluoro-5-iodo-pyridin-2-yl)-4,4-dimethyl-imidazolidin-2-one (205 mg, 49% yield) was obtained as a white solid, MS: m/e=336.1 (M+H+).

Workup

custompurified by flash chromatography
washeluting with an ethyl acetate

Sources & evidence

ORD record: ord-e8bd1007a9af4018b9066532510e7337
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420661B2

Reaction notes

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