5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide → 3-Acetyl-5-bromopyridine

HRID 1774850Notes

Reaction equation

HRID 1774850 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7](N(OC)C)=[O:8].[CH3:14][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[CH:13]=[C:6]([C:7](=[O:8])[CH3:14])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 8204233-Acetyl-5-bromopyridineYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-N-methoxy-N-methyl-nicotinamide (2.08 g, 8.5 mmol) in THF (20 mL) was added MeMgBr (1.52 g, 12.75 mmol) at −78° C. After the addition, the reaction mixture was stirred at room temperature for 2 hours before quenching with water. After extraction with EtOAC, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was then purified by flash column chromatography to afford the title compound (1.5 g, 88%).

Workup

  1. additionAfter the addition
  2. custombefore quenching with water
  3. extractionAfter extraction with EtOAC
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash column chromatography

Sources & evidence

ORD record
ord-a6ef9af66caa498b87b78c9f6f97aef9
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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