Sodium hydride → HCID 118599099, compound

HRID 1050425Notes

Reaction equation

HRID 1050425 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9](=[O:10])[NH:8][C:7]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[C:6]([CH3:17])[CH:5]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[Br:3][C:4]1[C:9](=[O:10])[N:8]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[C:7]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[C:6]([CH3:17])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 118598819HCID 118598819, compound

Product 1

HCID 118599099HCID 118599099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (2.5 mmol, 2.5 eq) to a cooled solution of 5-bromo-N-methoxy-N,3-dimethyl-6-oxo-1,6-dihydropyridine-2-carboxamide (2, 1.0 mmol, 1 eq) in dimethylformamide (25 mL) and stir the reaction for 20 min. Add 4-methoxybenzyl chloride (1.2 mmol, 1.2 eq) and stir the reaction for 16 h. After completion, quench the reaction with water and extract with ethyl acetate. Remove the solvent and purify the crude by column chromatography to afford 5-bromo-N-methoxy-1-(4-methoxybenzyl)-N,3-dimethyl-6-oxo-1,6-dihydropyridine-2-carboxamide (3).

Workup

  1. customthe reaction for 20 min
  2. customthe reaction for 16 h
  3. customAfter completion, quench
  4. customthe reaction with water
  5. extractionextract with ethyl acetate
  6. customRemove the solvent
  7. custompurify the crude by column chromatography

Sources & evidence

ORD record
ord-4e3419397eaf48c796fb0e1649128653
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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