Pyridine → 6-(2-Methyl-pyridin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094509Notes

Reaction equation

HRID 1094509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[C:20](Cl)[N:19]=[C:18]([CH3:23])N=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].N1C=CC=C[CH:25]=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:23]=[CH:18][N:19]=[C:20]([CH3:25])[CH:21]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 1049PyridineHCID 866651676-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Product 1

HCID 666408686-(2-Methyl-pyridin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

9.7 g (29.5 mMol) 6-(6-chloro-2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester in 950 ml THF and 24 ml (0.30 Mol) pyridine is hydrogenated in presence of 1.9 g Pd/C (10%, Engelhard 4505) during 15 h. The mixture is filtered, the solid washed extensively with THF and the filtrate concentrated. The residue is re-dissolved in EtOAc and 5% citric acid, the aq. layer separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated to the title compound: HPLC: tRet=12.8.

Workup

  1. filtrationThe mixture is filtered
  2. washthe solid washed extensively with THF
  3. concentrationthe filtrate concentrated
  4. dissolutionThe residue is re-dissolved in EtOAc
  5. custom5% citric acid, the aq. layer separated off
  6. extractionextracted with EtOAc
  7. washThe organic layers are washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to the title compound

Sources & evidence

ORD record
ord-f16d4615381f4ae99637d3077d3970af
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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