[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Br[CH2:14][C:15]#[CH:16].C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCCC.ClCCl>[CH2:16]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1)[C:15]#[CH:14]
A solution of 8.86 g (50 mmol) of 4-(trifluoromethoxy)benzenamine, 8.18 g (55 mmol) of an 80% solution of 3-bromo-1-propyne in toluene, and 8.72 ml (50 mmol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 200 ml of toluene is heated at 90° C. for eighteen hours. The suspension is cooled and treated with ethyl acetate. The suspension is washed several times with water. The ethyl acetate layer is separated, dried (magnesium sulfate), and concentrated to give a brown liquid. This is applied to a column of 1 kg of flash silica gel packed in n-heptane-dichloromethane (2:1). Elution with the same solvent gives 7.12 g (66.2%) of the product as a brown liquid.
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