Methanol → Methyl 4-[(pyridine-4-yl)methyl]benzoate

HRID 747694Notes

Reaction equation

HRID 747694 reaction equation
I[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][OH:23].[C]=O.CN(C)[CH:28]=[O:29]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]2[CH:13]=[CH:14][C:2]([C:22]([O:29][CH3:28])=[O:23])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 147430304-(4-Iodobenzyl)pyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 68834826Methyl 4-[(pyridine-4-yl)methyl]benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

1.03 g (3.49 mmol) of 4-(4-iodobenzyl)pyridine was dissolved in 15 ml of dimethylformamide. 39 mg (0.18 mmol) of palladium acetate, 0.97 ml (6.98 mmol) of triethylamine and 2.82 ml (69.8 mmol) of methanol were added to the solution, and the resultant mixture was stirred in the presence of carbon monoxide at 70° C. for 6 hours. The reaction solution was diluted with water. After the extraction with ethyl acetate, the organic layer was washed with water and then with a saturated Aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe organic layer was washed with water
  3. customThe solvent was evaporated
  4. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-58b58c96300149e7a829389adeeacf3b
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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