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

HRID 2218130Notes

Reaction equation

HRID 2218130 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].C(N(C(C)C)CC)(C)C.N1C=CC=CC=1.[CH2:32]([O:34][C:35]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)=[O:36])[CH3:33]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:32]([O:34][C:35](=[O:36])[CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([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:41][CH:40]=1)[CH3:33]

Participants

7

Reactant 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 38517004-(2-Ethoxycarbonylethyl)benzeneboronic acidHCID 541614103-(4-Nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 693003343-{4-[3-(4-Nitrophenyl)-2-oxo-2H-pyridin-1-yl]phenyl}propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(4-Nitrophenyl)-1H-pyridin-2-one (P3) (0.2 g, 0.92 mmol), copper (II) acetate (0.334 g, 2 equiv.), diisopropylethylamine (0.31 mL, 2 equiv.), and pyridine (0.15 mL, 2 equiv.) were added to a stirred solution of 4-(2-ethoxycarbonylethyl)phenyl boronic acid (0.308 g, 1.3 mmol) in dichloromethane (10 mL). The reaction mixture was then stirred under argon at room temperature for 4 hours. The solution was then filtered through celite, concentrated and purified by chromatography on silica gel (50% v/v ethyl acetate in hexane) to afford the title compound as an oil.

Workup

  1. filtrationThe solution was then filtered through celite,
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel (50% v/v ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4aa9d962a0e24c18bd33e83306bfd2b0
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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