[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]#[CH:12].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:12][C:11]#[CH:10])=[CH:4][CH:3]=1A solution of 9.47 ml (0.1 mol) of 4-fluorobenzenamine, 16.36 g (0.11 mol) of an 80% solution of 3-bromo-1-propyne in toluene, and 17.43 ml (0.11 mol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 350 ml of toluene is heated at 90° C. for three hours. Ethyl acetate is added to the reaction suspension, and it is washed three times with water. The organic layer is separated, dried (magnesium sulfate), and concentrated to give 15.5 g of a dark brown liquid. This is applied to a column of 1 kg of flash silica gel packed in heptane-dichloromethane (5:1). Elution with the same solvent gives 9.09 g (61%) of the product as a yellow oil.
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