6-Fluoro-N-methoxy-N-methylpyridine-3-carboxamide → 1-(6-Fluoropyridin-3-yl)ethan-1-one
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).