Benzyl Bromide → HCID 57467580, compound

HRID 1480830Notes

Reaction equation

HRID 1480830 reaction equation
[Br:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC#N.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:8][C:5]1[CH:4]=[C:3]([C:2]([Br:1])=[CH:7][N:6]=1)[C:9]([O:11][CH3:12])=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 25306972Methyl 5-bromo-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 57467580HCID 57467580, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of methyl 5-bromo-2-oxo-1,2-dihydropyridine-4-carboxylate (2.5 g, 10.77 mmol) in MeCN (35 mL) was added silver carbonate (4.46 g, 16.16 mmol) and benzyl bromide (1.54 mL, 12.93 mmol). The reaction mixture was heated to 65° C. and stirred for 18 hours. The reaction mixture was filtered through a plug of Celite® and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 50-100% DCM in cyclohexane to give the title compound (3.31 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite®
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with 50-100% DCM in cyclohexane

Sources & evidence

ORD record
ord-157e0f051f8d4e0e87db71f949b453a1
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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