[C:1]([C:3]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])#[CH:2].CO>[Pd]>[CH2:1]([C:3]1[N:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])[CH3:2]To a suspension of 2-ethynyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (145 mg, 0.561 mmol) in 5% Pd/C (30 mg) was added CH3OH (4 ml). The mixture was purged three times with hydrogen gas (50 psi) and shaken for 2 hours at room temperature. The reaction mixture was filtered over a pad of Celite and concentrated under reduced pressure. The crude residue was chromatographed to yield the 2-ethyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (112 mg, 76%).
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