Dimethylformamide → 1-[4-(2-bromoethoxy)phenyl]-4-[(5-chloro-2-pyridinyl)-methoxy]-1H-pyridin-2-one

HRID 15074

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:12](=[O:23])[CH:11]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:30][CH:31](Br)[CH3:32].CN(C=O)C>C(Cl)(Cl)Cl>[Br:30][CH2:31][CH2:32][O:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[CH:11][C:12]2=[O:23])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-hydroxyphenyl)-1H-pyridin-2-one (1.0 g, 3.1 mmols), cesium carbonate (5.0 g, 15 mmols), dibromoethane (5 mL) and DMF (10 mL) was stirred at 80° C. for 14.5 hours. Chloroform was added to the reaction liquid, followed by filtration. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (KP-Sil FLASH 25+ M, chloroform:methanol=1:0→100:2) to provide the title compound (1.2 g, 89%).

Workup

filtrationfollowed by filtration
concentrationConcentrating the solvent under reduced pressure
customthe residue was purified on silica gel column chromatography (KP-Sil FLASH 25+ M, chloroform:methanol=1:0→100:2)

Sources & evidence

ORD record: ord-7dec3d11c3284f1388bb76f0c9bc4e13
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732456B2

Linked notes

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