[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][C:12]([C:26]([F:29])([F:28])[F:27])([OH:25])[CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[CH3:24])([CH3:16])[CH3:15]>O1CCOCC1.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>[F:27][C:26]([F:29])([F:28])[C:12]([CH2:11][C:10]1[NH:1][C:2]2[C:3]([CH:9]=1)=[CH:4][CH:5]=[CH:6][C:7]=2[F:8])([OH:25])[CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[CH3:24])([CH3:15])[CH3:16]A solution of 1-(2-amino-3-fluorophenyl)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (900 mg, 2.2 mmol) in 10 mL of anhydrous dioxane was treated with dichlorobis(triphenylphosphine)palladium (II) (250 mg, 0.36 mmol) and the mixture was heated at 100° C. for 60 hours. The crude reaction mixture was purified on SiO2 (20% dichloromethane in hexanes) to afford 700 mg of the title product as a yellow oil (78% yield).
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