[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].BrC1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10]C=1[N+]([O-])=O.C([N:20]([CH2:23][CH3:24])CC)C.CN(C=[O:29])C.[OH2:30]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:14][C:12]1[CH:11]=[CH:10][C:24]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])=[C:23]([N+:20]([O-:29])=[O:30])[CH:13]=1To a flask charged with N,N-dimethylprop-2-yn-1-amine (737 mg, 945 μL, 8.86 mmol), 2-bromo-4-fluoro-1-nitrobenzene (1300 mg, 5.91 mmol), PdCl2(PPh3)2 (415 mg, 0.59 mmol), CuI (169 mg, 0.89 mmol) were added triethylamine (2.47 mL, 17.73 mmol) and DMF (10 mL) under N2 atmosphere. The reaction mixture was heated at 60° C. for 5 h, then poured into water (300 mL) and extracted with ethyl acetate (3×40 mL). The organic fractions were combined, dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50-100% ethyl acetate/hexanes) yielded 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine (895 mg, 68% yield). LC/MS m/z 223.0 [M+H]+.
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