Benzyl Bromide → HCID 57467580, compound

HRID 404313Notes

Reaction equation

HRID 404313 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>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

4

Reactant 2

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

Product 1

HCID 57467580HCID 57467580, compound

Reagents, catalysts & solvents 1

HCID 178418647HCID 178418647, compoundCatalyst

Conditions

Temperature
50 °C

Procedure

To 2 mL of methyl 5-bromo-2-oxo-1,2-dihydropyridine-4-carboxylate (232 mg, 1.00 mmol)(commercially available from Combi-Blocks) was added benzyl bromide (205 mg, 1.20 mmol) and silver carbonate (413 mg, 1.50 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The resulting mixture was stirred at 50° C. overnight. After reaction completion, the mixture was loaded onto a solid silica gel cartridge and purified by chromatography with 10% EtOAc/hexane to afford the desired product H6.1 (293 mg, 91%). MS ESI (pos.) m/e: 322.1 (M+H)+.

Workup

  1. customAfter reaction completion
  2. custompurified by chromatography with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-10704c18a97844e8860880e68ce57068
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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