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Methyl iodide → Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1696279
Notes
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Reaction equation

HRID 1696279 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:13])[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Product 1

HCID 59354302Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (1.5 g, 6.5 mmol) and potassium carbonate (0.99 g, 7.15 mmol) in DMF (25 mL) was stirred at room temperature for 15 min followed by the addition of methyl iodide (0.42 mL, 6.83 mmol). The resulting suspension was stirred at room temperature for 17 h. The mixture was partitioned between ethylacetate and water. The organic phase was separated and the aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over MgSO4 and concentrated to afford the title compound as a light yellow solid. MS m/z: 246 (M+1).

Workup

  1. stirringThe resulting suspension was stirred at room temperature for 17 h
  2. customThe mixture was partitioned between ethylacetate and water
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethylacetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ace606cb73b64ebda52f186d072b67c5
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163766B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes