Cesium carbonate → 3-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester

HRID 2218120Notes

Reaction equation

HRID 2218120 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:16])[NH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][CH:24]=1)[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][N:12]2[CH:13]=[CH:14][CH:15]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[C:11]2=[O:16])=[CH:27][CH:28]=1)[CH3:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11107077Ethyl 3-[4-(chloromethyl)phenyl]propanoateHCID 541614103-(4-Nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 693004653-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-ylmethyl]phenyl}propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Nitrophenyl)-1H-pyridin-2-one (P3, 200 mg, 0.93 mmol), 3-(4-chloromethyl-phenyl)propionic acid ethyl ester (P6, 270 mg, 1.20 mmol) and cesium carbonate (900 mg, 2.78 mmol) were stirred for 18 hours in dimethyl formamide (5 mL) at room temperature. The reaction mixture was filtered through celite (Diatomaceous Earth), concentrated and the crude mixture was purified by chromatography on silica gel (50% v/v ethyl acetate in petroleum ether) to afford the title compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite (Diatomaceous Earth)
  2. concentrationconcentrated
  3. customthe crude mixture was purified by chromatography on silica gel (50% v/v ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-bd696b99af21491bb6f00198778f7ed2
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

Loading…