HCID 53831436, compound → HCID 70023589, compound

HRID 398381Notes

Reaction equation

HRID 398381 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11](=[O:22])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCO>[C:1]1(/[CH:7]=[CH:8]\[C:9]2[CH:14]=[C:13]([CH3:15])[N:12]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11](=[O:22])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 53831436HCID 53831436, compound

Product 1

HCID 70023589HCID 70023589, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-phenylethynyl-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 3 above (1.5 g, 4.6 mmol) and Lindlar catalyst (5%Pd on CaCO3 plus Pb;150 mg) in EtOH (25 mL) was stirred under an atmosphere of hydrogen at ambient pressure and temperatue for 1 h. The catalyst was removed by filtration and the filtrate solvent was removed in vacuo to give the title compound as a mixture containing 20% of the fully saturated (phenethyl) derivative (1.5 g; TLC Rf=0.5, 1:1 EtOAc:hexanes; HPLC RT=8.15 min, method A).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate solvent was removed in vacuo

Sources & evidence

ORD record
ord-fb35cab89a0640ddb0f1b747ea0d9cbe
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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