Benzyl Bromide → HCID 67483868, compound

HRID 1357467Notes

Reaction equation

HRID 1357467 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[NH:7][C:6]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:7][C:6]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 11687512HCID 11687512, compound

Product 1

HCID 67483868HCID 67483868, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalyst3×HCID 1140TolueneSolvent

Procedure

A slurry of 2-benzoyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester (1.00 g), benzyl bromide (1.88 ml) and silver carbonate (1.64 g) in toluene (50 ml) was stirred at room temperature in the dark under nitrogen for 3 days. More silver carbonate (0.82 g) was added and the slurry was stirred as before for 24 h. A final portion of silver carbonate (0.82 g) was added, and the mixture was stirred as before for 3 days. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane, yielding 2-benzoyl-6-benzyloxynicotinic acid methyl ester as a pale brown solid (1.14 g). 1H NMR (400 MHz, CDCl3) δ3.69 (3H, s), 5.39 (2H, s), 6.92 (1H, d, J=8.8 Hz), 7.30 (3H, m), 7.37 (2H, m), 7.45 (2H, t, J=7.7 Hz), 7.59 (1H, t, J=7.4 Hz), 7.78 (2H, d, J=7.8 Hz), 8.25 (1H, d, J=8.7 Hz); MS (ES+) m/e 348 [MH]+.

Workup

  1. stirringthe mixture was stirred as before for 3 days
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ef0dedf532744d27b8c211cf618149d2
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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