6-Fluoro-N-methoxy-N-methylpyridine-3-carboxamide → 1-(6-Fluoropyridin-3-yl)ethan-1-one

HRID 75954Notes

Reaction equation

HRID 75954 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][N:3]=1.[CH3:14][Mg]Br>C1COCC1>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:6](=[O:7])[CH3:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 587671286-Fluoro-N-methoxy-N-methylpyridine-3-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-oneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution (−78° C.) of 6-fluoro-N-methoxy-N-methylnicotinamide (Method 38, 7.2 g, 39 mmol) in THF (130 ml), was added methyl magnesium bromide (20 ml, 59 mmol, 3M solution in ether) dropwise. The cooling bath was removed and reaction mixture was allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with 3N HCl solution, layers were cut, and organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford 3.8 g (70% yield) of the title compound. 1H NMR (CDCl3) δ 8.80 (s, 1H) 8.29-8.43 (m, 1H) 6.98-7.06 (m, 1H) 2.62 (s, 3H).

Workup

  1. customThe cooling bath was removed
  2. customreaction mixture
  3. customThe reaction was quenched with 3N HCl solution, layers
  4. dry with materialorganic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-815ab5d22e3a4621bbf2ecced962cf93
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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