[OH:1][C:2]1[C:3]([C:12]#[N:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[NH2:13][C:12]1[C:3]2[CH:4]=[C:5]3[C:10]([CH:9]=[CH:8][CH:7]=[CH:6]3)=[CH:11][C:2]=2[O:1][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:17]To a stirred solution of 3-hydroxy-naphthalene-2-carbonitrile from step 2 (200 mg, 1.18 mmol) and 2,2′,4′-trichloroacetophenone (317 mg, 1.42 mmol, 1.2 eq) in anhydrous N,N-dimethylformamide (4.7 mL) was added potassium carbonate (326.7 mg, 2.36 mmol, 2.0 eq), and the orange reaction mixture was stirred at 80° C. for 16 h. The resulting dark wine colored reaction was diluted with ethyl acetate and water. The organic layer was washed with saturated aqueous ammonium chloride, water, brine, and dried over magnesium sulfate. The solvent was removed at reduced pressure and the crude product was purified on the MPLC (biotage) eluted with 15% ethyl acetate-hexane. Crystallization from ether-hexane afforded 243 mg (57.7%) of the desired benzofuran. 1H-NMR (DMSO-d6) δ 8.66 (s, 1H), 7.99 (d, J=8.1 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.88 (s, 1H), 7.76 (d, J=1.5 Hz, 1H), 7.72 (broad s, 2H), 7.63 to 7.42 (m, 4H); LC-MS (ES MH+=356).
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