Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([O:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5]2.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1B(O)O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([O:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5]2Following the procedure described in Step 1 of Example 1, 2-[(6-bromo-1-chloro-2-naphthyl)oxy]acetonitrile (9.7, 33 mmol) was coupled to 2-benzofuranboronic acid (6.35 g, 39 mmol), in the presence of[1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1:1) (1.40 g, 1.71 mmol) and potassium carbonate (9.13 g, 66.1 mmol) in dioxane (330 mL) and water (3.3 mL). Purification by flash chromatography using 5-30% ethyl acetate in hexane and 7.5-50% ethyl acetate in hexane as eluants yielded 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetonitrile as a light brown solid (6.13 g), mp 162-163° C. 1HNMR (300 MHz, DMSO-d6): δ8.55 (s, 1H), 8.15-8.25 (m, 3H), 7.65-7.75 (m, 3H), 7.6 (s, 1H), 7.25-7.4 (m, 2H), and 5.45 ppm (s, 2H).
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