HCID 67209520, compound → HCID 67209404, compound

HRID 402505Notes

Reaction equation

HRID 402505 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]([CH3:17])=[CH:7][N:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][C:8]([CH3:17])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 67209520HCID 67209520, compound

Product 1

HCID 67209404HCID 67209404, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-Methoxycarbonyl-vinyl)-5-methyl-pyridine-2-carboxylic acid methyl ester (2.58 g, 10.97 mmol) was dissolved in MeOH (100 ml) and hydrogenated at rt with Pd/C (10%, Engelhard 4505, 1.20 g) and 1.0 bar H2 for 1 h. The reaction was filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica (hex to hex/EtOAc 2/3 in 40 min) to give the product as colorless oil (2.33 g, 90%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.34 (s, 1H), 7.65 (s, 1H), 3.84 (s, 3H), 3.58 (s, 3H), 3.03 (t, 2H), 2.63 (t, 2H), 2.33 (s, 3H); LCMS RtI=2.786 min; [M+H]+=238.0.0]

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by chromatography on silica (hex to hex/EtOAc 2/3 in 40 min)

Sources & evidence

ORD record
ord-35ba470367b049ed89501fe22075dc77
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

Loading…