[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:22]=[CH:21][C:20]([CH:23]([OH:27])[CH2:24][CH2:25][CH3:26])=[CH:19][C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[OH:27][CH:23]([C:20]1[CH:19]=[C:16]([C:17]#[N:18])[C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[CH:22][CH:21]=1)[CH2:24][CH2:25][CH3:26]A sealed flask was charged with the (4-(trifluoromethyl)phenyl)boronic acid (1.09 g, 5.76 mmol), 2-bromo-5-(1-hydroxybutyl)benzonitrile (1.33 g, 5.23 mmol) and acetonitrile (17 mL). Once everything get into solution, 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (115 mg, 157 μmol) was added followed by the sodium carbonate 2M aq. (6.54 mL, 13.1 mmol). Flask sealed and heated at 140° C. for 1 hour. Organic solvent removed under reduced pressure and ethyl acetate added. Organics washed with water (1×), with brine (1×), dried over sodium sulfate, filtered and concentrated to provide the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/Heptane) provide the title compound as a colorless oil (1.39 g, 83.2%). 1H NMR (400 MHz, DMSO-d6) δ 0.87-0.93 (m, 3H) 1.25-1.45 (m, 2H) 1.57-1.67 (m, 2H) 4.64-4.70 (m, 1H) 5.41 (d, J=4.68 Hz, 1H) 7.64 (d, J=8.00 Hz, 1H) 7.75-7.79 (m, 1H) 7.82 (d, J=8.00 Hz, 2H) 7.88-7.94 (m, 3H).
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